DOCSLIB.ORG

A Three-Step Sequence Strategy for Facile Construction of Donor-Acceptor Type Molecules: Triphenylamine- Substituted Acenes

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
A Three-Step Sequence Strategy for Facile Construction of Donor-Acceptor Type Molecules: Triphenylamine- Substituted Acenes Canadian Journal of Chemistry A Three-step Sequence Strategy for Facile Construction of Donor-Acceptor Type Molecules: Triphenylamine- Substituted Acenes Journal: Canadian Journal of Chemistry Manuscript ID cjc-2019-0254.R1 Manuscript Type: Article Date Submitted by the 21-Sep-2019 Author: Complete List of Authors: Zhang, Chen; Wuhan University of Technology, chemical Engineering and Life Sciences Tang, Ming; Wuhan University of Technology, chemical Engineering and Life SciencesDraft Sun, Bing; Wuhan University of Technology, chemical Engineering and Life Sciences Wang, Weizhou; Wuhan University of Technology, chemical Engineering and Life Sciences Yi, Ying; Wuhan University of Technology, chemical Engineering and Life Sciences Zhang, Fang-Lin; Wuhan University of Technology, chemical Engineering and Life Sciences Is the invited manuscript for consideration in a Special Not applicable (regular submission) Issue?: Keyword: triphenylamine, anthracene, C–H activation, fluorescence https://mc06.manuscriptcentral.com/cjc-pubs Page 1 of 14 Canadian Journal of Chemistry 1 A Three-step Sequence Strategy for Facile Construction of Donor-Acceptor Type Molecules: Triphenylamine-Substituted Acenes Chen Zhang, Ming Tang, Bing Sun, Weizhou Wang, Ying Yi and Fang-Lin Zhang Chen Zhang, Ming Tang, Bing Sun, Ying Yi and Fang-Lin Zhang. chemical Engineering and Life Sciences, Wuhan University of Technology, Wuhan 430070, Hubei, PR China. Weizhou Wang. College of Chemistry and Chemical Engineering, and Henan Key Laboratory of Function-Oriented Porous Materials, Luoyang Normal University, Luoyang 471934, PR China. Corresponding authors: Weizhou Wang (e-mail: [email protected]), Ying Yi (e-mail: [email protected]) and Fang-Lin Zhang (e-mail: [email protected]) Draft https://mc06.manuscriptcentral.com/cjc-pubs Canadian Journal of Chemistry Page 2 of 14 2 Abstract: A new synthetic strategy was successfully developed for highly efficient construction of triphenylamine-substituted polycyclic aromatic hydrocarbons (PAHs), including anthracenes, tetraphenes, pentaphenes and trinaphthylene. These molecules exhibited special structural characteristics, including donor-acceptor-donor (D-A-D) and donor-acceptor (D-A). Diverse aryl iodides coupled well with chlorinated 2-methyl benzaldehydes via a transient ligand-directed C–H bond arylation strategy to furnish various PAH precursors. The subsequent palladium-catalyzed Suzuki cross-couplings with 4-(diphenylamino)phenylboronic acid produced corresponding triphenylamine derivatives. Further Brønsted acid-promoted cycloaromatization generated the triphenylamine-substituted PAHs readily. The photophysical properties was investigated by UV-visible absorption and fluorescence emission spectroscope together with density functional theory (DFT) calculations. Key words: triphenylamine, anthracene, C–H activation, fluorescence. Draft https://mc06.manuscriptcentral.com/cjc-pubs Page 3 of 14 Canadian Journal of Chemistry 3 Introduction Due to their unique molecular structure and optical property, organic conjugated molecules bearing donor–acceptor (D-A) system are widely used as photoelectron materials in the area of organic solar cells, organic light-emitting diodes (OLEDs), sensors, data storage displays and organic crystal field-effect transistors (OFETs) etc1-6. The diverse combinations of various donor and acceptor moieties endow these systems easily tunable highest occupied molecular orbital (HOMO) energy levels and lowest unoccupied molecular orbital (LUMO) energy levels, adjustable optical bandgap, large π-conjugation length, intramolecular charge transfer and strong π-π stacking interactions5,7, which contribute to the readily tunable optical and electrical properties of the hole-transporting materials (HTMs). Triphenylamine (TPA) group proves to be a widely used donor unit for construction of opto- and electroactive organic small molecules and polymeric materials since it has good electron donating and hole-transporting property as well as special nonplanar propeller starburst molecular shape8-10. Polycyclic aromatic hydrocarbons (PAHs), such as anthracenes11, phenanthrenes12, pyrenes13 and tetracenes14, exhibit excellent fluorescence characteristics and have been introduced into the D- A system to improve the photoelectric properties like color purity and electroluminescence (EL) efficiency of materials15. Literature survey showed that a variety of D-A configuration molecules with TPA as donor moiety and PAHs as acceptor moieties have been prepared. For instance, in 2016, Putala group6 reported a series of D-A system molecules featuring TPA and analogues connecting to different positions of the aromatic ring cores by alkyne. In 2017, Hariharan etc.16 synthesized a set of twisting D-A molecules with TPA as donor, aromatic hydrocarbons include benzene (Ph), naphthalene (Nap), anthracene (An), phenanthrene (Phe) and pyrene (Py) as acceptor via the Suzuki-Miyaura cross-couplings with aryl (Ph, Nap, An, Phe and Py) boronic acids. The dual-core derivatives of TPA end-capped anthracence and pyrene were also constructed using two-step Suzuki couplings13,15. Furthermore, the TPA unit cooperated with PAHs were applied to build copolymer macromolecules through coupling interactions17. Most of them used anthracene as core and introduced TPA moiety into the C-9 and/or C-10 positions by Suzuki-Miyaura couplings starting from commercially available halogenated polyacenes18-26. However, other polycyclic segments are rarely utilized because of the expensive costs or exhausting synthetic processes of PAHs, especially with extensive fused aromatic rings14,27. To circumvent the above limitations, our previous work developed a highly efficient two-step strategy to readily construct PAHs28,29 (Scheme 1). The first step proceeded via a transient directing group enabled palladium-catalyzed ortho-C(sp3)–H arylation of benzaldehydes, while the second step involvedDraft a Brønsted acid-promoted cycloaromatization27,30. In this work, D- A-D and D-A arrays end-capped with one or more TPA as donor units were elaborately designed and facilely synthesized. The highly efficient cascade arylations and cycloaromatizations of Our previous work: O I 1) Pd(OAc)2 via: transient DG O I N O I 2) TfOH Pd H OAc This work: Donor Donor R R I O 1) Pd(OAc)2 transient DG I TPA4BA I 2) cross-coupling Cl 3) TfOH Donor R Donor: R = N N Scheme 1. Synthesis of TPA derivatives. benzaldehydes with halides provided a series of PAHs, including anthracene, tetraphene, pentaphene and trinaphthylene, which served as acceptor units. Particularly, the trinaphthylene molecule as a central core decorated with three TPA groups at 2, 8 and 14-positions formed a special nonplanar propeller star-shaped structure31. Result and Discussion Synthesis of donor-acceptor type molecules Based on our previous work, a new three steps synthetic route to prepare TPA derivatives with polyacene core was developed28,29. First, a transient directing group enabled palladium-catalyzed ortho-C(sp3)–H arylation of benzaldehyde 6 with iodobenzenes afforded the precursor 7. Subsequent Suzuki cross-couplings with 4-(diphenylamino)phenylboronic acid (TPA4BA) produced corresponding triphenylamine derivatives 8. Further cycloaromatization by treatment with trifluoromethanesulfonic acid (TfOH) generated TPA derivatives with D-A array. TPA derivatives combined with anthracene core were widely utilized as organic functional materials3,19. However, those previous anthracene derivatives mainly restricted on the highly reactive C-9 or C-10 position of anthracene32. Herein, we obtained new anthracene derivatives with TPA group on the C-2 or C-6 position (Scheme 2). These derivatives contain electron-donating group (methyl) and electron withdrawing group (chloride). Furthermore, the chloride substituent allowed readily derivatizations via cross-coupling reactions. Then, this new three-step sequence strategy were further extended to the synthesis of tetraphene derivatives. By using of 2- iodonaphthalene as coupling partner, D-A molecule 2a and the acceptor tetraphene was successfully synthesized (Scheme 3). The tetracene derivatives with methyl at C-9 position (2b) was also obtained in good yield. https://mc06.manuscriptcentral.com/cjc-pubs Canadian Journal of Chemistry Page 4 of 14 4 To further explore the substrate scope, 1,4-diiodobenzene was examined to construct TPA derivatives bearing a pentaphene segment (Scheme 4). The D-A-D molecule 3a with pentaphene core was constructed by using TfOH as cycloaromatization reagent. In addition, D-A-D molecules with TPA groups on C-1, C-12 and C-2, C-10 positions (3b & 3c) were also successfully incorporated. Pd(OAc) O 2 O AgTFA I glycine X AcOH/H2O (v/v=9/1) X 1 R1 (70%-74%) R 5 6 7 1 O R TPA4BA TfOH 2 cross-coupling R (54%-73%) 1 (56%-73%) R R2 8 1 N N 1a 1b Cl N 1c Scheme 2. Synthesis of TPA derivatives with anthracene as acceptor unit. O Pd(OAc)2 O AgTFA I glycine H (Br) H (Br) AcOH/H2O (v/v=9/1) Cl (Me) (72%-73%) Cl (Me) 5 6 7 Draft O (Me) R TPA4BA TfOH cross-coupling H (R) (70%-77%) (68%) R (Me) H (R) 8 2 N N 2a 2b Scheme 3. Synthesis of TPA derivatives with tetraphene as acceptor unit. Pd(OAc) O 2 AgTFA I (Me)Cl O glycine Cl(Me) I AcOH/H2O (v/v=9/1) (Me)Cl (52%-66%) O 5 6 7 R R O TPA4BA O TfOH R cross-coupling R (80%-82%) (66%-85%) 8 3 N N N 3a N N N 3c 3b Scheme 4. Synthesis of TPA derivatives with pentaphene as acceptor unit. https://mc06.manuscriptcentral.com/cjc-pubs Page 5 of 14 Canadian Journal of Chemistry 5 Recently, star-shaped π-conjugated
Load more

Recommended publications
  • Polycyclic Aromatic Hydrocarbon Structure Index
    NIST Special Publication 922 Polycyclic Aromatic Hydrocarbon Structure Index Lane C. Sander and Stephen A. Wise Chemical Science and Technology Laboratory National Institute of Standards and Technology Gaithersburg, MD 20899-0001 December 1997 revised August 2020 U.S. Department of Commerce William M. Daley, Secretary Technology Administration Gary R. Bachula, Acting Under Secretary for Technology National Institute of Standards and Technology Raymond G. Kammer, Director Polycyclic Aromatic Hydrocarbon Structure Index Lane C. Sander and Stephen A. Wise Chemical Science and Technology Laboratory National Institute of Standards and Technology Gaithersburg, MD 20899 This tabulation is presented as an aid in the identification of the chemical structures of polycyclic aromatic hydrocarbons (PAHs). The Structure Index consists of two parts: (1) a cross index of named PAHs listed in alphabetical order, and (2) chemical structures including ring numbering, name(s), Chemical Abstract Service (CAS) Registry numbers, chemical formulas, molecular weights, and length-to-breadth ratios (L/B) and shape descriptors of PAHs listed in order of increasing molecular weight. Where possible, synonyms (including those employing alternate and/or obsolete naming conventions) have been included. Synonyms used in the Structure Index were compiled from a variety of sources including “Polynuclear Aromatic Hydrocarbons Nomenclature Guide,” by Loening, et al. [1], “Analytical Chemistry of Polycyclic Aromatic Compounds,” by Lee et al. [2], “Calculated Molecular Properties of Polycyclic Aromatic Hydrocarbons,” by Hites and Simonsick [3], “Handbook of Polycyclic Hydrocarbons,” by J. R. Dias [4], “The Ring Index,” by Patterson and Capell [5], “CAS 12th Collective Index,” [6] and “Aldrich Structure Index” [7]. In this publication the IUPAC preferred name is shown in large or bold type.
    [Show full text]
  • Hexaazatriphenylene (HAT) Derivatives. from Synthesis to Molecular Design, Self-Organization and Device Applications
    Chemical Society Reviews Hexaazatriphenylene (HAT) derivatives. From synthesis to molecular design, self-organization and device applications Journal: Chemical Society Reviews Manuscript ID: CS-SYN-02-2015-000181.R2 Article Type: Review Article Date Submitted by the Author: 25-Jun-2015 Complete List of Authors: Segura, Jose; Universidad Complutense, Quimica Organica I Juárez, Rafael; Universidad Rey Juan Carlos, Department of Environmental and Technological Chemistry Ramos, María del Mar; Universidad Rey Juan Carlos, Department of Environmental and Technological Chemistry Seoane, Carlos; Universidad Complutense, Quimica Organica I Page 1 of 34Journal Name Chemical Society Reviews Dynamic Article Links ► Cite this: DOI: 10.1039/c0xx00000x www.rsc.org/xxxxxx ARTICLE TYPE Hexaazatriphenylene (HAT) derivatives. From synthesis to molecular design, self-organization and device applications Jose Luis Segura, a* Rafael Juarez, a,b Mar Ramos b and Carlos Seoane a 5 Received (in XXX, XXX) Xth XXXXXXXXX 20XX, Accepted Xth XXXXXXXXX 20XX DOI: 10.1039/b000000x Dipyrazino[2,3-f:2',3'-h]quinoxaline also known as 1,4,5,8,9,12-hexaazatriphenylene ( HAT ) is an electron deficient, rigid, planar, aromatic discotic system with an excellent π-π stacking ability. Because it is one of the smallest two-dimensional N-containing polyheterocyclic aromatic systems, it has been used as the basic scaffold for larger 2D N-substituted polyheterocyclic aromatics. 10 Furthermore, it is the building block of choice in a plethora of molecular, macromolecular and supramolecular systems for a variety of applications. This review is aimed to critically review the research performed during the almost three decades of research based on HAT from the synthetic, theoretical and applications point of view.
    [Show full text]
  • WO 2016/074683 Al 19 May 2016 (19.05.2016) W P O P C T
    (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2016/074683 Al 19 May 2016 (19.05.2016) W P O P C T (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every C12N 15/10 (2006.01) kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, (21) International Application Number: BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, PCT/DK20 15/050343 DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (22) International Filing Date: HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, 11 November 2015 ( 11. 1 1.2015) KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, (25) Filing Language: English PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, (26) Publication Language: English SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (30) Priority Data: PA 2014 00655 11 November 2014 ( 11. 1 1.2014) DK (84) Designated States (unless otherwise indicated, for every 62/077,933 11 November 2014 ( 11. 11.2014) US kind of regional protection available): ARIPO (BW, GH, 62/202,3 18 7 August 2015 (07.08.2015) US GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, (71) Applicant: LUNDORF PEDERSEN MATERIALS APS TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, [DK/DK]; Nordvej 16 B, Himmelev, DK-4000 Roskilde DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, (DK).
    [Show full text]
  • IUPAC Provisional Recommendations
    Preferred IUPAC Names 73 Chapter 2, Sect 25 September, 2004 P-25 Fused and bridged fused systems P-25.0 Introduction P-25.1 Names of hydrocarbon components P-25.2 Names of heterocyclic components P-25.3 Constructing fusion names P-25.4 Bridged fused systems P-25.5 Limitations to fusion nomenclature: three components ortho- and peri- fused together P-25.6 Heteroatoms in nonstandard valence states P-25.7 Treatment of double bonds and δ-convention P-25.8 List of fusion components in decreasing order of seniority P-25.0 Introduction This section is based on the document entitled ‘Nomenclature of Fused and Bridged Fused Ring System, IUPAC Recommendations 1998’ (ref. 4). In nomenclature, fusion is the operation that creates a common bond between two rings, each ring contributing one bond and the two atoms directly attached to the bond. This type of fusion is called ortho- or ortho- and peri-fusion if two adjacent bonds are involved. The term fusion is also used todesc ribe the operation creating a common atom between two ring systems, each contributing one atom. This type of fusion is called spirofusion (see P-24.1). Traditionally, ortho- and ortho- and peri-fusion were simply called fusion and the resulting polycyclic systems were referred to as fused ring systems or fused ring compounds. The term 'spirofusion' is new in nomenclature, and to avoid ambiguity 'fusion' should not be used without the prefix 'spiro' when 'spirofusion' is intended." CH HC C + CH HC C benzene (PIN) benzene (PIN) naphthalene (PIN) [naphthalene results from the fusion
    [Show full text]
  • Polycyclic Organic Compounds, Polarizing
    (19) TZZ ZZ¥_T (11) EP 2 260 035 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: C07D 471/04 (2006.01) C07D 487/04 (2006.01) 20.08.2014 Bulletin 2014/34 C07D 487/22 (2006.01) C07D 495/16 (2006.01) C07C 15/38 (2006.01) (21) Application number: 09717753.9 (86) International application number: (22) Date of filing: 04.03.2009 PCT/GB2009/050218 (87) International publication number: WO 2009/109781 (11.09.2009 Gazette 2009/37) (54) POLYCYCLIC ORGANIC COMPOUNDS, POLARIZING ELEMENTS AND METHOD OF PRODUCTION THEREOF POLYCYCLISCHE ORGANISCHE VERBINDUNGEN, POLARISIERUNGSELEMENTE UND VERFAHREN ZU DEREN HERSTELLUNG COMPOSÉS ORGANIQUES POLYCYCLIQUES, ÉLÉMENTS POLARISANTS ET LEUR PROCÉDÉ DE FABRICATION (84) Designated Contracting States: • DATABASE CAPLUS [Online] CHEMICAL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR ABSTRACTS SERVICE, COLUMBUS, OHIO, US; HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL 7 October 2007 (2007-10-07), XP002543542 PT RO SE SI SK TR retrieved from STN Database accession no. 2007: 1167020 & VAKULIN, I. V. ET AL.: "Quantum- (30) Priority: 04.03.2008 GB 0804082 chemical study of formation of complexes of aromatic Schiff bases with transition metals (43) Date of publication of application: using the UB3LYP/3-21G(d) approximation" 15.12.2010 Bulletin 2010/50 BASHKIRSKII KHIMICHESKII ZHURNAL, vol. 14, no. 1, 2007, pages 124-128, Bashkir State (73) Proprietor: CRYSOPTIX K.K. University, Ufa; RU ISSN: 0869-8406 Tokyo (JP) • LIANG, B. ET AL.: "HIGH-EFFICIENCY RED PHOSPHORESCENT IRIDIUM DENDRIMERS (72) Inventors: WITH CHARGE-TRANSPORTING DENDRONS: • NOKEL, Alexey SYNTHESIS AND ELECTROLUMINESCENT Moscow 119619 (RU) PROPERTIES" ADVANCED FUNCTIONAL • LAZAREV, Pavel I.
    [Show full text]
  • IUPAC Nomenclature of Fused and Bridged Fused Ring Systems
    Pure &App/. Chern., Vol. 70, No. 1, pp. 143-216, 1998. Printed in Great Britain. Q 1998 IUPAC INTERNATIONAL UNION OF PURE AND APPLIED CHEMISTRY ORGANIC CHEMISTRY DIVISION COMMISSION ON NOMENCLATURE OF ORGANIC CHEMISTRY (111.1) NOMENCLATURE OF FUSED AND BRIDGED FUSED RING SYSTEMS (IUPAC Recommendations 1998) Prepared for publication by G. P. MOSS Department of Chemistry, Queen Mary and Westfield College, Mile End Road, London, El 4NS, UK Membership of the Working Party (1982-1997): A. T. Balaban (Romania), A. J. Boulton (UK), P. M. Giles, Jr. (USA), E. W. Godly (UK), H. Gutmann (Switzerland), A. K. Ikizler (Turkey), M. V. Kisakiirek (Switzerland), S. P. Klesney (USA), N. Lozac’h (France), A. D. McNaught (UK), G. P. Moss (UK), J. Nyitrai (Hungary), W. H. Powell (USA), Ch. Schmitz (France), 0. Weissbach (Federal Republic of Germany) Membership of the Commission on Nomenclature of Organic Chemistry during the preparation of this document was as follows: Titular Members: 0. Achmatowicz (Poland) 1979-1987; J. Blackwood (USA) 1996; H. J. T. Bos (Netherlands) 1987-1995, Vice-chairman, 1991- ; J. R. Bull (Republic of South Africa) 1987-1993; F. Cozzi (Italy) 1996- ; H. A. Favre (Canada) 1989-, Chairman, 1991- ; P. M. Giles, Jr. (USA) 1989-1995; E. W. Godly (UK) 1987-1993, Secretary, 1989-1993; D. Hellwinkel (Federal Republic of Germany) 1979-1987, Vice-Chainnan, 1981-1987; B. J. Herold (Portugal) 1994- ; K. Hirayama (Japan) 1975-1983; M. V. Kisakiirek (Switzerland) 1994, Vice-chairman, 1996- ; A. D. McNaught (UK) 1979-1987; G. P. Moss (UK) 1977-1987, Chairman, 1981-1987, Vice-chairman, 1979-1981; R.
    [Show full text]
  • Nanonewsletter No
    nanonewsletter No. 28 /// December 2013 www.phantomsnet.net AtMol Special Issue Electron tunnelling manipulation of self- assembled molecular nanostructures Coronene: A Single Molecule Atom Counter Measuring the conductance of single molecular wires as a function of the electron energy Synthesis of Y-Shaped Polyarenes, Crushed Fullerenes and Nanographene Fragments dear readers, Dear Readers, The AtMol Integrated Project (EU/ICT/FET) is currently establishing a comprehensive process flow for fabricating a molecular chip, i.e. a molecular processing unit comprising a single molecule connected to external mesoscopic electrodes with atomic scale precision and preserving the integrity of the gates down to the atomic level after the encapsulation. This E-nano Newsletter special issue contains four articles providing new insights on this hot research topic in Europe, in particular for the fabrication of future generations of electronic circuits with components miniaturized down to atomic scale. Detailed information about the project, further reading documents and AtMol workshop series contributions could be found at www.atmol.eu. We would like to thank all the authors who contributed to this issue as well as the European Commission for the financial support (ICT/FET FP7 AtMol project no. 270028). > Dr. Antonio Correia Editor - Phantoms Foundation contents 05 > nanoresearch - AtMol. Electron tunnelling manipulation of self-assembled molecular nanostructures /// F. Moresco, A.Nickel, R. Ohmann, J. Meyer, M. Grisolia, C. Joachim and G.Cuniberti 13 > nanoresearch - AtMol. Coronene: A Single Molecule Atom Counter /// C. Manzano, W. H. Soe, M. Hliwa, M. Grisolia, H. S. Wong and C. Joachim 21 > nanoresearch - AtMol. Measuring the conductance of single molecular wires as a function of the electron energy /// M.Koch, F.
    [Show full text]
  • Voltage/ 33O Current Source U.S
    US007 18301 OB2 (12) United States Patent (10) Patent No.: US 7,183,010 B2 Jarikov (45) Date of Patent: Feb. 27, 2007 (54) ORGANIC LIGHT-EMITTING DIODE (58) Field of Classification Search ................ 428/690, DEVICES WITH IMPROVED OPERATIONAL 428/917; 313/504,506 STABILITY See application file for complete search history. (75) Inventor: Viktor V. Jarikov, Rochester, NY (US) (56) References Cited (73) Assignee: Eastman Kodak Corporation, U.S. PATENT DOCUMENTS Rochester, NY (US) 5,281,489 A * 1/1994 Mori et al. .... ... 428,690 5,294.870 A * 3/1994 Tang et al. ....... ... 313,504 (*) Notice: Subject to any disclaimer, the term of this 5,405,709 A * 4/1995 Littman et al. ... ... 428,690 patent is extended or adjusted under 35 6,740,429 B2 * 5/2004 Aziz et al. ........ ... 428,690 U.S.C. 154(b) by 58 days. 2004/0021415 A1* 2/2004 Vong et al. ................. 313,509 (21) Appl. No.: 10/634,324 * cited by examiner Primary Examiner Dawn Garrett (22) Filed: Aug. 5, 2003 (74) Attorney, Agent, or Firm—Raymond L. Owens (65) Prior Publication Data (57) ABSTRACT US 2004/0076853 A1 Apr. 22, 2004 An organic light-emitting device includes a Substrate, an Related U.S. Application Data anode and a cathode disposed over the Substrate, and a (63) Continuation-in-part of application No. 10/131,801, luminescent layer disposed between the anode and the filed on Apr. 24, 2002, now abandoned. cathode wherein the luminescent layer includes a host and at least one dopant. The host of the luminescent layer is (51) Int.
    [Show full text]
  • Downloaded for Personal Non-Commercial Research Or Study, Without Prior Permission Or Charge
    https://theses.gla.ac.uk/ Theses Digitisation: https://www.gla.ac.uk/myglasgow/research/enlighten/theses/digitisation/ This is a digitised version of the original print thesis. Copyright and moral rights for this work are retained by the author A copy can be downloaded for personal non-commercial research or study, without prior permission or charge This work cannot be reproduced or quoted extensively from without first obtaining permission in writing from the author The content must not be changed in any way or sold commercially in any format or medium without the formal permission of the author When referring to this work, full bibliographic details including the author, title, awarding institution and date of the thesis must be given Enlighten: Theses https://theses.gla.ac.uk/ [email protected] THE SYNTHESIS and STUDY of POLYCYCLIC AROMATIC HYDROCARBONS. THESIS presented by John Fergus Stephen, B.Sc. (Glasgow) for the degree of DOCTOR OF PHILOSOPHY of the University of Glasgow* October, 19&4* ProQuest Number: 10984191 All rights reserved INFORMATION TO ALL USERS The quality of this reproduction is dependent upon the quality of the copy submitted. In the unlikely event that the author did not send a com plete manuscript and there are missing pages, these will be noted. Also, if material had to be removed, a note will indicate the deletion. uest ProQuest 10984191 Published by ProQuest LLC(2018). Copyright of the Dissertation is held by the Author. All rights reserved. This work is protected against unauthorized copying under Title 17, United States C ode Microform Edition © ProQuest LLC.
    [Show full text]
  • Controlling the Edges: from Nanographenes Towards to Graphene Nanoribbons
    Controlling the Edges: From Nanographenes Towards to Graphene Nanoribbons Dissertation zur Erlangung des Grades „Doktor Der Naturwissenschaften“ im Fachbereich Chemie, Pharmazie, und Geowissenschaften der Johannes Gutenberg--‐Universität Mainz und in Kooperation mit dem Max-Planck-Institut für Polymerforschung Mainz vorgelegt von Junzhi Liu geboren in Sichuan/China Mainz, 2015 Dekan: Prof. Dr. Wolfgang Tremel 1. Berichterstatter: Prof. Dr. Klaus Müllen 2. Berichterstatter: Prof. Dr. Rudolf Zentel Tag der mündlichen Prüfung: 14.01.2016 Die vorliegende Arbeit wurde in der Zeit von July 2011 bis January 2015 im Max- Planck-Institut für Polymerforschung in Mainz unter der Betreuung von Prof. Dr. Klaus Müllen durchgeführt. Ich danke Prof. Dr. Klaus Müllen für seine wissenschaftliche und persönliche Unterstützung sowie für seine ständige Diskussionsbereitschaft. My parents, wife and daughter Table of Contents Chapter 1. Introduction ...................................................................................... 1 1.1 PAH with armchair-edged structure ............................................................ 6 1.2 PAH with cove-edged structure ................................................................ 10 1.3 PAH with zigzag-edged structure ............................................................. 14 1.4 Unconventional PAHs .............................................................................. 21 1.4.1 Open-shell Polycyclic Hydrocarbons .............................................. 21 1.4.2 Antiaromatic Indenofluorenes
    [Show full text]
  • Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics
    Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics. This journal is © the Owner Societies 2017 Structural Information (indication of number or Topological Information (Number of Edge Group and Ring Types) Results 5-membered Armchai Aromati Empty HOMO-LUMO BE Avg Molecule Name Carbons Hydrogens Rings Rings Aliphatics r Zigzag Free Edge Bay Fjord c Sextets Rings Dbl(1) Dbl(2) Gap (eV) (kJ/mol) benzene 6 6 1 0 N 0 0 6 0 0 1 0 0 0 8.0444 ethynylbenzene 8 6 1 0 Y 0 0 7 0 0 1 0 0 0 5.4968 styrene 8 8 1 0 Y 0 0 7 0 0 1 0 0 0 5.4447 1_3-diethynylbenzene 10 6 1 0 Y 0 0 8 0 0 1 0 0 0 5.2591 1_4-diethynyl-2- vinylbenzene 12 8 1 0 Y 0 0 9 0 0 1 0 0 0 4.51 1_3-diethynyl-5- vinylbenzene 12 8 1 0 Y 0 0 9 0 0 1 0 0 0 5.0386 naphthalene 10 8 2 0 N 0 2 6 0 0 1 0 0 1 4.6722 1_1'-biphenyl 12 10 2 0 Y 0 0 12 0 0 2 0 0 0 5.2148 -38.05 1-vinylnaphthalene 12 10 2 0 Y 0 2 7 0 0 1 0 0 1 4.1595 2-vinylnaphthalene 12 10 2 0 Y 0 2 7 0 0 1 0 0 1 4.2733 acenaphthylene 12 8 3 1 N 0 3 5 0 0 1 0 1 1 4.1133 5-vinylacenaphthylene 14 10 3 1 Y 0 3 6 0 0 1 0 1 1 3.748 4-vinylacenaphthylene 14 10 3 1 Y 0 3 5 0 0 1 0 1 1 3.8584 4- 14 8 3 0 Y 0 3 6 0 0 1 0 1 1 3.891 3- 14 8 3 1 Y 0 3 6 0 0 1 0 1 1 3.8822 anthracene 14 10 3 0 N 0 4 6 0 0 1 0 0 2 3.5087 -48.71 phenanthrene 14 10 3 0 N 1 2 7 0 0 2 0 1 0 4.3985 -44.49 2-phenylnaphthalene 16 12 3 0 Y 0 2 12 0 0 2 0 0 1 4.3678 -38.47 1-ethynyl-8- vinylacenaphthylene 16 10 3 1 Y 0 3 7 0 0 1 0 1 1 3.5406 3-ethynyl-8- vinylacenaphthylene 16 10 3 1 Y 0 3 7 0 0 1 0 1 1 3.5764 4_7- divinylacenaphthylene 16 12
    [Show full text]
  • PAH Charge State Distribution and DIB Carriers: Implications from the Line of Sight Toward HD 147889,
    A&A 432, 515–529 (2005) Astronomy DOI: 10.1051/0004-6361:20040331 & c ESO 2005 Astrophysics PAH charge state distribution and DIB carriers: Implications from the line of sight toward HD 147889, R. Ruiterkamp1,N.L.J.Cox2,M.Spaans3, L. Kaper2,B.H.Foing4,F.Salama5, and P. Ehrenfreund2 1 Leiden Observatory, PO Box 9513, 2300 RA Leiden, The Netherlands e-mail: [email protected] 2 Institute Anton Pannekoek, Kruislaan 403, 1098 SJ Amsterdam, The Netherlands 3 Kapteyn Astronomical Institute, PO Box 800, 9700 AV Groningen, The Netherlands 4 ESA Research and Scientific Support Department, PO Box 299, 2200 AG Noordwijk, The Netherlands 5 Space Science Division, NASA Ames Research Center, Mail Stop 245-6, Moffett Field, California 94035, USA Received 25 February 2004 / Accepted 29 September 2004 Abstract. We have computed physical parameters such as density, degree of ionization and temperature, constrained by a large observational data set on atomic and molecular species, for the line of sight toward the single cloud HD 147889. Diffuse interstellar bands (DIBs) produced along this line of sight are well documented and can be used to test the PAH hypothesis. To this effect, the charge state fractions of different polycyclic aromatic hydrocarbons (PAHs) are calculated in HD 147889 as a function of depth for the derived density, electron abundance and temperature profile. As input for the construction of these charge state distributions, the microscopic properties of the PAHs, e.g., ionization potential and electron affinity, are determined for a series of symmetry groups. The combination of a physical model for the chemical and thermal balance of the gas toward HD 147889 with a detailed treatment of the PAH charge state distribution, and laboratory and theoretical data on specific PAHs, allow us to compute electronic spectra of gas phase PAH molecules and to draw conclusions about the required properties of PAHs as DIB carriers.
    [Show full text]