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Polycyclic Hydrocarbons Volume 2 To Sir Robert Robinson Polycyclic Hydrocarbons E. CLAR University of Glasgow, Scotland With a chapter on Carcinogenesis by REGINA SCHOENT AL Medical Research Council, Cm"shaltan Surrey, England VOLUME 2 1964 Springer-Verlag Berlin Heidelberg GmbH ACADEMIC PRESS INC. (LONDON) LTD Berkeley Square House Berkeley Square London, W.1 ISBN 978-3-662-01670-1 ISBN 978-3-662-01668-8 (eBook) DOI 10.1007/978-3-662-01668-8 U.S. Edition published by ACADEMIC PRESS INC. 111 Fifth Avenue New York 3, New York Copyright © 1964 By SPRINGER-VERLAG BERLIN HEIDELBERG ORTGINALL Y PUBLTSHED BY ACADEMIC PRESS INC. (LONDO:t'<) LTD IN 1964 AU Rights Reserved No part ofthis book may be reproduced in any form, by photostat, microfilm, or any othcr means, without written permission from the publishers Library of Congress Catalog Card Number: 63-12392 Preface Polycyclic hydrocarbons are of interest in many fields of science: theoretical chemistry, physical chemistry, organic chemistry, dyestuff chemistry and biology. With regards to the latter, I am indebted to Dr. Regina Schoental of the Medical Research Council for the review in this present work of carcinogenesis by polycyclic hydrocarbons. This book is designed to present the facts in a simple and clear order and to derive empirical rules from them, but it does not present a com­ prehensive theory about polycyclic hydrocarbons. An attempt is made instead to extend classical symbolism into modern structural chemistry. Thus extensive use is made of Robinson's aromatic sextet, which is applied in an uncompromising and strict way. This quasi-classical attempt is encouraged further by such completely unexpected dis­ coveries as those of Dewar benzene and of the electronic asymmetry of formally symmetric hydrocarbons. How difficult it is to break away from any established way of thinking has been admirably expressed by Kekule ("Organische Chemie", 1861, Part 1, page 4, translated from German): "All our ideas are based, to an extent much greater than we ordinarily believe, on those of our predecessors. Our accumulated experience, the notions of which our training has accustomed us to, of whatever kind they have been, influence the course of our thoughts far more than we are willing to admit; only too frequently the following of our regularly used, well trodden way of thinking leads to us overlook the simplest of correlations. " Great emphasis has been given to the comparison of the physical properties of polycyclic hydrocarbons, and in this work as in future research, I have been and shall be guided by another declaration of Kekule ("Organische Chemie", Part 1, page 158): "Of course it must be continually kept in mind that one purpose of scientific research is to ascertain the constitution of matter and therefore the positions of atoms; this, however, cannot be achieved unambiguously by studying chemical reactions but on the contrary, only by comparing the physical properties of the existing compounds." I am indebted to my colleagues Dr. T. H. Goodwin, Dr. J. C. Speakman and Dr. F. Schwarz for valuable advice and help and to Dr. A. McCallum and Mr. J. Stephen for checking the proofs. I also greatly appreciate the efforts of Academic Press to meet my wishes. E. CLAR University of Glasgow April 1964 v Contents PART III peri-Condensed Hydrocarbons consisting only of Six-membered Rings and derived from Fundamental Systems with Two Benzenoid Rings CHAPTER 28. Hydrocarbons derived from Diphenyl: I. Diphenyl i~1 ~/ I:) . 3 II. Fluorene ~ I I ~/\ I CH 2 ~/ I I ~ ..... 6 III. Biphenylene ~-/"f I~/I_I~ .. 11 IV. 1.2-Benzobiphenylene I~_I~/i-Ji ..................... 15 V. 2.3-Benzobiphenylene I-I~~ ~)-~~) ... 17 vii VIll CONTENTS VI. 1.2,7.8-Dibenzobiphenylene 18 VII. 2. 3,6. 7-Dibenzobiphenylene O:)~:) .... 19 VIII. Tetraphenylene, Hexaphenylene and Octaphenylene (1_(1 O-Q I~( (I :C~C ~\ /~ I~/I (J vl)~~ 22 CHAPTER 29. Hydrocarbons derived from Perylene: I. Perylene rI~1 &S 24 CONTENTS ix II. 1.2-Benzoperylene 36 III. 2.3-Benzoperylene 40 IV. 1.2,7.8-Dibenzoperylene rI~~ ~~ 1",)~~0 .... 42 V. 1.2,l0.1l-Dibenzoperylene ~;::I ~~~~ . .. 46 VI. 1.2,11.12-Dibenzoperylene rI~O 47 sII-a* ............ x CONTENTS VII. 1.2,5.6-Dibenzoperylene I~I~I ~/~ I I /~/~~~ I~/~~/~/ I I I I .................. 51 VIII. 1.2,5.6,7.S,11.12-Tetrabenzoperylene I~I/~I/I~I "--/~/~r~ I I I~I/~I/"--I~I ~/~/~/~/ . ., 52 IX. 2.3,S. 9-Dibenzoperylene X. 2.3,lO.1l-Dibenzoperyleno 56 CONTENTS XI XI. Dinaphtho-(2'.3': 2.3); (2".3": 8.9)-perylene I~I ""(I ""~/"1 I I I ""/~ I I III ~~(~ L) 59 XII. 1.12-Benzoperylene ~~ I I I ~/~/~ 111/I I I ~/~ ...................... 60 XIII. 1.12,2.3-Dibenzoperylene ~~ I I I ~~/~ I I I /~/~/ I I I ~/~/~ l) ......... 63 XIV. 1.12,2.3,8.9-Tribenzoperylene II ~/~/~ I I I ""/"1~ I I I /~(~/ ! I ~~/~ I I ~/ ................... 65 xii CONTENTS xv. 1.12,2.3,10.11-Tribenzoperylene V"----/"----~ &6 .................... 66 XVI. 1.12,4.5,8.9-Tribenzoperylene ~ I"----)~l I I~ )yl~ I I rI~/ ~ ........................ 69 XVII. 1.12,5.6,7 .8-Tribenzoperylene rI~11 ~YYI ~~~/ I I I I "----/~~ ................... 71 72 CONTENTS xiii XIX. Anthraceno-( 1',4' :1.12)-perylene !I~I YY"("(i III~~/ ~~ ..................•..•• 73 XX. 1.12-0-Phenylene-2.3-benzoperylene 1:):)"(,, I I ) III~ ~Y"I ,,/ ...... • . • • . •• 75 XXI. 1.12-0-Phenylene-2.3,10 .11-dibenzoperylene 76 XXII. 1.2,3.4,5.6,10.11-Tetrabenzanthanthrene 78 xiv CONTENTS XXIII. Coronene /~(X~ ~ I I I I ~(yy ~~/ ..................... 79 XXIV. 1.2-Benzocoronene 86 XXV. 1.2,5.6-Dibenzocoronene /'- /~/II ~;C~ i I I I Y~./~/I I ~~I~I ~/ .................. " 88 XXVI. 1.2,7.8-Dibenzocoronene /~/~ rI~I~~1 ~~/~/~/~/ I~/~/ I I ................... 90 CONTENTS xv XXVII. 1.2,3.4,5.6-Tribenzocoronene (yy Cf(YO ~~/~ 1~ 1 .................... 92 XXVIII. Naphtho-(2'.3' :1.2)-coronene /~'---.... 1 I I II/'---....I/'---....I~I~I ~/'---..../~/'---..../'---..../ 1 I~/~/ I ..................... 94 XXIX. 1.12,2.3,4.5,6.7,8.9,10.11-Hexabenzocoronene (I I/'''-I~I/I~I ~('---..../'---....(~/ I I I !/'---....I/I/I 0'---....('---..../~ ~) ..................... 95 CHAPTER 30. Hydrocarbons derived from Bisanthene: I. Bisanthene I/'---....i/'---....I/~I '---....(I/Y 1/'---....1/'---....11 ~/'---..../'---..../ .................... 98 XVI CONTENTS II. 1.14-Benzobisanthene 07\ ~. 100 III. Ovalene IV. 3.4, 10. ll-Dibenzobisanthene and 3.4,1 I. 12-Dibenzobisanthene V. 1.2,3.4,8.9,10.1l-Tetrabenzobisanthene /~ c/I~ oYX~yY0 ~/ ................... 107 CONTENTS xvii VI. Circumanthracene 108 CHAPTER 31. Hydrocarbons derived from Pyrene: I. Pyrene (I 1('''-1 "-/~ l) ....................... llO II. 1.2-Benzopyrene ~ l)'~ . 127 III. 3.4-Benzopyrene (I 9 "- 130 IV. 1.2,3.4-Dibenzopyrene T~~ I,,-/. 1 . 141 XVlll CONTENTS V. 1.2,4.5-Dibenzopyrene /~ I I /~/~/~ I I I I !?/~ ~ ......... 145 VI. 1.2,6.7-Dibenzopyrene /~ /~/l/l~ I I I I I ~/~/~/~/ I I ~/ ... .. 148 VII. 3.4,8.9-Dibenzopyrene /~ I I ~/~ I I I/~I/~I '-,,/~/ I I ~/~ I I f} ~ ........ .. I I VIII. 3.4,9.10-Dibenzopyrene I~I /~/ I I /~/~ I I I ~/~/ I I ~~ I~/ I ....................... 153 CONTENTS XIX IX. 1.2,4.5,8.9-Tribenzopyrene ~ ¢y~ /~/ I~ I ......................... 157 X. 1.2,3.4,9.10-Tribenzopyrene /~ )~) I I I~~~ I I ~(I ~/ ...................... 160 XI. 1.2,3.4,6.7,8.9-Tetrabenzopyrene . .. 162 xx CONTENTS XII. Naphtho-(2'.3' :1.2)-pyrene cy=o(i l/ ........... 163 XIII. Naphtho-(I'.2': 3.4)-pyrene dI(" lX~ I~~I ....... 165 XIV. Naphtho-(2'.3': 3.4)-pyrene /" /l/I" I,,/,,/ I I I I If,,) ........... 166 XV. 1.2-Benzonaphtho-(2".3": 4.5)-pyrene 01 -))"XA/ O. 169 CONTENTS xxi XVI. 1.2-Benzonaphtho-(21 .3": 6.7)-pyrene ~~~/" 1~1""/J0,,,/J0 I"'/ I . .. 171 XVII. 8.9-Benzonaphtho-(21 .1":3.4)-pyrene and 3.4-Benz­ anthraceno-(2 1 .1": 8.9)-pyrene C) ) . 173 XVIII. 3.4-Benzonaphtho-(21 .3": 8.9)-pyrene C)::c:C) '" l~X/I ...... .. 174 XIX. 3.4-Benzonaphtho-(21 .3": 9.10)-pyrene E I~ L:~ I",/. I . .. 175 xxn CONTENTS xx. Dinaphtho-(2'.3' :1.2); (2".3" :4.5)-pyrene ~ /I~)~~/~ I I I I I ~/~/~~/ I I /y/~/ u. .. 177 XXI. Dinaphtho-(2'.3' :1.2); (2".3": 6.7)-pyrene (X):XXXJ(~ l) ................... 179 XXIII. Dinaphtho-(2'.3': 3.4); (2".3": 9.10)-pyrene /() /~)~) I I I (I~(I(I/ u~/~~ ................. 182 CONTENTS XXUl XXIV. 1.2-Benzodinaphtho-(2" .3": 4.5); (2" .3": 8. 9)-pyrene /~ ~) /0"l) I I I I~I~I/II/ ~/~~~/~ I~/ I ................. 183 XXV. 1.14,4.5-Dibenzopentacene /~ I I I/~I/~!/~I/~Iy~ ~~/~/'-y/ l/ ... " .......... 185 XXVI. Naphtho-(I'.7': 2.14)-pentacene /~/~ I I I l/I/~I/~I/I~I/ ~~~/~~/. 186 XXVII. Phenanthreno-(2' .3': 3.4)-pyrene ~~ I I I I,/~(~(~(~/ . I I/~I~/~~/ ~ ......................... 188 XXVIII. 1.2-Benzophenanthreno-(9'.10': 6.7)-pyrene /~ /~ I I I I ~~~~/ I I I I I ~/~/~/~/~ I~/ I I~/ I ................. 190 xxiv CONTENTS XXIX. 1.2,3.4,6.7, 12. 13-Tetrabenzopentacene (I / o:;cD " ~) ,,) . 191 XXX. 1.16,4.5-Dibenzohexacene (I CXXXX?J . .. 192 . 194 XXXII. Naphtho-(I'.7': 2. 16)-hexacene (Y" CI/"~/"~(") I I I I ~~~~~. ......... 195 XXXIII. 6.7,16.17-Dibenzoheptacene (I (I~I~('I~II ~"/"/YI/~"/ ,,/ . .. 197 XXXIV. 5.6,8.9,14.15,17.18-Tetrabenzoheptacene (I (I rII~('Y"I~(I ~YY"/YI/ ,,/ ,,/ ........... 198 CONTENTS XXV xxxv. 1.18,4.5,9.10,13.14-Tetrabenzoheptacene /~ (~ I~~/~/~~~~/~ l) I~) ...........
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    THATTHE TOUT UNTUK USU 20180134954A1ROMAW ATU TO NIKALI HINTHI ( 19) United States (12 ) Patent Application Publication ( 10) Pub . No. : US 2018 /0134954 A1 TSAI et al. (43 ) Pub . Date : May 17 , 2018 ( 54 ) ORGANIC ELECTROLUMINESCENT Related U . S . Application Data MATERIALS AND DEVICES (63 ) Continuation - in -part of application No . 15 /407 ,337 , (71 ) Applicant : Universal Display Corporation , filed on Jan . 17 , 2017 . Ewing , NJ (US ) (60 ) Provisional application No .62 / 293 ,100 , filed on Feb . 9 , 2016 , provisional application No. 62 / 338 ,616 , filed (72 ) Inventors : Jui- Yi TSAI, Newtown, PA (US ) ; on May 19 , 2016 . Chuanjun XIA , Lawrenceville , NJ (US ) ; Chun LIN , Yardley, PA (US ) ; Publication Classification Adrian U . PALACIOS , Zaragoza (ES ) ; (51 ) Int. CI. Enrique OÑATE , Zaragoza (ES ) ; CO9K 11 /06 (2006 .01 ) Miguel A . Esteruelas , Zaragoza (ES ) ; CO7F 15 / 00 ( 2006 . 01 ) Pierre -Luc T . BOUDREAULT , HOIL 51/ 00 (2006 .01 ) Pennington , NJ (US ); Sonia BAJO , 2 ) U . S . CI. Zaragoza (ES ) ; Montserrat OLIVÁN , CPC . C09K 11 /06 ( 2013 . 01 ) ; HOIL 51 /5016 Zaragoza (ES ) (2013 . 01 ) ; HOIL 51/ 0085 ( 2013 .01 ) ; CO7F ( 73 ) Assignee : Universal Display Corporation , 15/ 0033 (2013 . 01 ) Ewing , NJ (US ) (57 ) ABSTRACT Novel Iridium complexes having three different bidentate ( 21 ) Appl. No .: 15 / 866 , 561 ligands useful for phosphorescent emitters in OLEDs are disclosed . At least one of the three different bidentate ligands (22 ) Filed : Jan . 10 , 2018 is a carbene ligand . ) www Patent Application Publication May 17, 2018 Sheet lof7 US 2018 / 0134954 A1 ** “ ? ,,, MMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMM M MMMM * * * mmmmmmmmmmmmmmmmmmmmmmmmmmmmmmmmmm &s??????8 … … … … … * * . ) Ht - ? FIG ? 1 Patent Application Publication May 17 , 2018 Sheet 2 of 7 US 2018 / 0134954 A1 ????? ????? ????? ????? ??? ?????? ???????? ????? ????? ???????? ????? ????? ?????? ??? ?? ????? ????? ????? ????? ???? ????? ???? ?? ? FIG .
  • IUPAC Nomenclature of Fused and Bridged Fused Ring Systems

    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.
  • Recent Progress in Quinoidal Singlet Biradical Molecules

    Recent Progress in Quinoidal Singlet Biradical Molecules

    Received: November 2, 2014 | Accepted: November 21, 2014 | Web Released: November 29, 2014 CL-140997 Highlight Review Recent Progress inQuinoidal Singlet Biradical Molecules Takashi Kubo Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043 (E-mail: [email protected]) Takashi Kubo was born in Yamaguchi, Japan, in 1968. He graduated from Osaka University in 1991, received M.Sc. in 1993 under the guidance of Professor Ichiro Murata, and received Ph.D. in 1996 under the guidance of Professor Kazuhiro Nakasuji.After working at Mitsubishi Chemical Co., he joined Professor Nakasuji’s group at Department of Chemistry, Graduate School of Science, Osaka University in 2000 as Assistant Professor. In 2006 he served as Associate Professor. Since 2006 he is Professor of Graduate School of Science, Osaka University. He received the Bulletinof the Chemical Society of Japan Award in 2001. His research interests are structural and physical organic chemistry, mainly the syntheses and properties of polycyclic aromatic compounds with open-shell character, and the development of multifunctional materialsusing a cooperative proton- and electron-transfer system. Chem. Lett. 2015, 44, 111–122 | doi:10.1246/cl.140997 © 2015 The Chemical Society of Japan | 111 Abstract Ph Ph Ph Ph Elusive nature inspin state isafeature of singlet biradical Ph Ph Ph Ph molecules and arises from the weak coupling of unpaired 2 l i i li i f i e ectrons. Th shgh ght rev ew ocuses on recent advances n i i i i ’ f l f experimental approaches for elucidating the electronic structure F gure 2.
  • Extension to Nanographenes with Zig-Zag Edges

    Extension to Nanographenes with Zig-Zag Edges

    ARTICLE DOI: 10.1038/s41467-018-07095-z OPEN Dehydrative π-extension to nanographenes with zig-zag edges Dominik Lungerich 1,2, Olena Papaianina1, Mikhail Feofanov 1, Jia Liu3, Mirunalini Devarajulu3, Sergey I. Troyanov4, Sabine Maier 3 & Konstantin Amsharov 1 Zig-zag nanographenes are promising candidates for the applications in organic electronics due to the electronic properties induced by their periphery. However, the synthetic access to 1234567890():,; these compounds remains virtually unexplored. There is a lack in efficient and mild strategies origins in the reduced stability, increased reactivity, and low solubility of these compounds. Herein we report a facile access to pristine zig-zag nanographenes, utilizing an acid-promoted intramolecular reductive cyclization of arylaldehydes, and demonstrate a three-step route to nanographenes constituted of angularly fused tetracenes or pentacenes. The mild conditions are scalable to gram quantities and give insoluble nanostructures in close to quantitative yields. The strategy allows the synthesis of elusive low bandgap nanographenes, with values as low as 1.62 eV. Compared to their linear homologues, the structures have an increased stability in the solid-state, even though computational analyses show distinct diradical character. The structures were confirmed by X–ray diffraction or scanning tunneling microscopy. 1 Department of Chemistry and Pharmacy, Organic Chemistry II, Friedrich-Alexander-University Erlangen-Nuernberg, Nikolaus-Fiebiger-Str. 10, 91058 Erlangen, Germany. 2 Department of Chemistry & Molecular Technology Innovation Presidential Endowed Chair, University of Tokyo, 7-3-1 Hongo, Bunkyo- ku, Tokyo 113-0033, Japan. 3 Department of Physics, Friedrich-Alexander-University Erlangen-Nuernberg, Erwin-Rommel-Str. 1, 91058 Erlangen, Germany. 4 Chemistry Department, Moscow State University, Leninskie Gory, Moscow, Russia 119991.