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(12) United States Patent (10) Patent No.: US 9.249,071 B2 Strauss Et Al US009249071B2 (12) United States Patent (10) Patent No.: US 9.249,071 B2 Strauss et al. (45) Date of Patent: Feb. 2, 2016 (54) MODIFIED POLYAROMATIC Bravo, “New Methods of Free-Radical Periluoroalkylation of Aro HYDROCARBONS AND matics and Alkenes. Absolute Rate Constants and Partial Rate Factors POLYHETEROCYCLICS FOR for the Homolytic Aromatic Substitution by n-Perfluorobutyl Radi OPTOELECTRONICS cal”, J. Org. Chem., 21:7128-7136 (1997). Cowell, “Fluoroalkylation of Aromatic Compounds”, Journal of (71) Applicant: Colorado State University Research Fluorine Chemistry, 17:345-356 (1981). Foundation, Fort Collins, CO (US) Freskos, "A Convenient Synthesis of Pentafluoroethyl-substituted Aromatics”, Journal: Synthetic communications, 18(9):965-972 (72) Inventors: Steven H. Strauss, Fort Collins, CO (1988). (US): Olga V. Boltalina, Fort Collins, Hosokawa et al., “Synthesis of Beta-Trifluoromethylnaphthalene CO (US); Igor V. Kuvychko, Fort Derivatives'. Gov't Industrial Research Institute, 2:383-386 (1972). Collins, CO (US) (With English Abstract). Hosokawa et al., “Synthesis of (Trifluoromethyl)naphthalenes', (73) Assignee: Colorado State University Research Gov't Industrial Research Institute, 11:1791-1793 (1976). (With Foundation, Fort Collins, CO (US) English Abstract). Hosokawa et al., “Synthesis Bis(trifluoromethyl)naphthalenes', (*) Notice: Subject to any disclaimer, the term of this Gov't Industrial Research Institute, 8: 1163-1167 (1977). (With patent is extended or adjusted under 35 English Abstract). U.S.C. 154(b) by 0 days. Hosokawa et al., “Synthesis of Substituted (Trifluoromethyl)naphthalenes', Gov't Industrial Research Institute, (21) Appl. No.: 14/174,780 2:294-296 (1979). (With English Abstract). Krespan et al., “Bis-(polyfluoroalkyl)-acetylenes. II. (22) Filed: Feb. 6, 2014 Bicyclooctatrienes Through 1,4-Addition of Bis-(polyfluoroalkyl)- acetylenes to Aromatic Rings'. Synthesis of Bicyclooctatrienes, (65) Prior Publication Data Contribution No. 648 from the Central Research Department, US 2014/0221 655A1 Aug. 7, 2014 Experimental Station, 83:3428-3432 (1961). Klebachet al., “Compounds Containing Localized Carbon-Phospho rus Double Bonds I. Diels-Alder Reaction of 3-Methyl-2- Phosphanaphtahlene with Hexafluorobutyne-2. Pergamon Press, Related U.S. Application Data Tetrahedron Letters 12:1099-1 100 (1978). (60) Provisional application No. 61/761,528, filed on Feb. Kuvychko et al., “Taming Hot CF3 Radicals: Incrementally Tuned 6, 2013. Families of Polyarene Electron Acceptors for Air-Stable Molecular Optoelectronics'. Angew. Chem. Int. Ed, 52:4871-4874 (2013). (51) Int. Cl. (Continued) CO7D 47L/04 (2006.01) C07C 17/32 (2006.01) CD7C 22/08 (2006.01) Primary Examiner — Heidi Reese C07C 22/02 (2006.01) (74) Attorney, Agent, or Firm — Haukaas Fortius PLLC; (52) U.S. Cl. Michael H. Haukaas CPC ................. C07C 17/32 (2013.01); C07C22/02 (2013.01); C07C 22/08 (2013.01); C07C 2102/30 (2013.01); C07C 2103/24 (2013.01); (57) ABSTRACT C07C 2103/26 (2013.01); C07C 2103/42 (2013.01); C07C 2103/52 (2013.01) The invention provides methods for substituting polyaro (58) Field of Classification Search matic hydrocarbons or polyheterocyclic compounds with None perfluoroalkyl groups. The methods can include heating a See application file for complete search history. polyaromatic hydrocarbon Substrate or a polyheterocyclic (56) References Cited compound Substrate in the presence of a perfluoroalkyl iodide, typically in a closed system, wherein the heating is U.S. PATENT DOCUMENTS sufficient to bring both the polyaromatic hydrocarbons or 3,281.426 A * 10/1966 Van Dyke Tiers ............ 540,140 polyheterocyclic compound, and the perfluoroalkyl iodide, 7,390,901 B2 6/2008 Yang into the gas phase, thereby allowing the Substrate to react with 2012/0208989 A1 8, 2012 Sun the perfluoroalkyl iodide in the gas phase to form polyaro FOREIGN PATENT DOCUMENTS matic hydrocarbons or polyheterocyclic compounds having one or more perfluoroalkyl substituents. The methods allow WO 2011/022678 A1 2, 2011 for the creation of versatile libraries of novel perfluoroalkyl OTHER PUBLICATIONS containing derivatives that can serve as important building blocks and active components in biomedical, electronic, and Dunyashev et al., Additivity of Electron-Affinity in a Series of Aro materials applications. matic-Compounds During the Accumulation of Fluoroalkyl Substituents Based on Polarography and Theoretical Calculations of the MNDO Method. 19 Claims, 22 Drawing Sheets US 9.249,071 B2 Page 2 (56) References Cited TunableOptoelectronic and Electron Transfer Properties”. J. Phys. Chem. A., 116:8015-8022 (2012). OTHER PUBLICATIONS Tiers, “Perfluoroalkylation of Aromatic Compounds”. Communica tions to the Editor JACS, Contribution No. 182 from the Central Roy et al., “Tetrahedron report No. 933: Trifluoromethylation of aryl Research Dept of 3M, pp. 5513 (1960). and heteroaryl halides”, Tetrahedron, 67:2161-2195 (2011). Sun et al., “Arene Trifluoromethylation: An Effective Strategy to Obtain Air-Stable n-Type Organic Semiconductors with * cited by examiner U.S. Patent Feb. 2, 2016 Sheet 1 of 22 US 9.249,071 B2 Figure 1 U.S. Patent Feb. 2, 2016 Sheet 2 of 22 US 9.249,071 B2 photoaiector Sg8ia as TRPH-6-1a PYRN-6- grger gram binding energy, ev Figure 2 Y-K-8-2 Yrxis. cycic: woitataragrass Ev vs, Fe(Cp)." Figure 3 U.S. Patent Feb. 2, 2016 Sheet 3 of 22 US 9.249,071 B2 FERYCF, 8 0 1 2 3 4 5 6 7 number of CF groups, in Figure 4 Aji Cis s .38. s 6 -38 (.8 8 . .3, FA}} or PA-(CF) electron affinity, ev Figure 5 U.S. Patent Feb. 2, 2016 Sheet 4 of 22 US 9.249,071 B2 *:: 8 PYRN-5- Y&N.S. U.S. Patent Feb. 2, 2016 Sheet 5 of 22 US 9.249,071 B2 CC COOee fluorene fluoranthene naphthalene anthracene tetracene phenanthrene pentacene perylene pyrene aZulene biphenylene triphenylene acenaphthylene phenalene chrysene picene aS-indacene Figure 7 U.S. Patent Feb. 2, 2016 Sheet 6 of 22 US 9.249,071 B2 S. M FN N N aCridine phenanthroline phenanthridine N 1. CCO CCON N phenazine phenothiazine O)N COOH H iminodibenzyl indole (10,11-dihydro-5H-dibenz(b,f)azepine) isoquinoline N21 N nS1 NS N n 1. N-2 1. N1 N 4H-quinolizine quinoline 1,7-phenanthroline CON OCN 9H-Carbazole beta-Carboline Figure 8 U.S. Patent Feb. 2, 2016 Sheet 7 of 22 US 9.249,071 B2 CF C2F5 CF r S of: SrcF, scF. CF NAPH(CFs). C2F5 NAPH (CFs). CF7 Cafe of, s-s ch s ea re, a\ a Cafg CF7 NAPH(n-CF). Cafs NAPH (n-C4Fo)4 Figure 9 U.S. Patent Feb. 2, 2016 Sheet 8 of 22 US 9.249,071 B2 Figure 9 (cont) U.S. Patent Feb. 2, 2016 Sheet 9 of 22 US 9.249,071 B2 y: 3537; + 337888x Rs: (.3333; y: 0.4743 - 3.3884x R: 3.98888 3,3 a 2.5- AN : &les - YRN is squares 5 2.0 t (3 ... 3 15 1,3- c S 0.5 / ANTH slopes 0.38 ev per CF. group &R is PYRK siege as 3.39 ev per CF group Faber of CF3 groups, in Figure 10 rworrorM 88 8Si 330 33 s rfg Figure 11 U.S. Patent Feb. 2, 2016 Sheet 10 of 22 US 9.249,071 B2 8A-C, 8.8 3.3 8. 8:88::::::::::::... g.:8: 8:38::::::::::::::::::::::: Figure 12 U.S. Patent Feb. 2, 2016 Sheet 11 of 22 US 9.249,071 B2 6. 33.4. Figure 13 U.S. Patent Feb. 2, 2016 Sheet 12 of 22 US 9.249,071 B2 Figure 14 U.S. Patent Feb. 2, 2016 Sheet 13 of 22 US 9.249,071 B2 Figure 15 U.S. Patent Feb. 2, 2016 Sheet 14 of 22 US 9.249,071 B2 NAPHR), R. A Cas A -/2 - NA w3. o-2 -1.0 E, v vs. Fe(Cp)," Figure 16 U.S. Patent Feb. 2, 2016 Sheet 15 of 22 US 9.249,071 B2 *F NMR in CDC, AZ-3-3 AX-3-2 A2-3- a li zults | A2.4-2 --------------------------------------------------Aas -54 -56 -58 -60 -62 -64 -66 ppm Figure 17 R in 3. A s --------------------------------H NMR in CDC, A **-tir'-----------------------------------------was----------------------------------A23-3-3 is ; : -------a------a-a-a-a-- '....... non-a-a-a-a---------------------------------------------------------- 'WA.--------------a----------------'aws--------Air' real-a---------------------s---- --- it -- - -------------------------------------------------------------------------- 9.3 3. S. Q 8.8 88 8.4 8.2 38 7.8 ppi Figure 18 U.S. Patent Feb. 2, 2016 Sheet 16 of 22 US 9.249,071 B2 O 2.0 3.O 4.O binding energy, eV Figure 19 U.S. Patent Feb. 2, 2016 Sheet 17 of 22 US 9.249,071 B2 5-5, s 3. assa 'tis essa...e. er kgy, &... e-estsa. ... : gy 'ssites ex . 3.61. A &xxx8c:-3&33 & Espá; : g ho-isfl. y s 8X k “, s' 8. 8. w & Figure 20 U.S. Pa tent Feb. 2, 2016 Sheet 18 of 22 US 9.249,071 B2 AZULENE(CF3), r C10Hs-n(CFs) it Chemical Name Structure formula AZUL- C3H5Fo i3.5- 3- AZUL(CFs): 3.6- azulene(CF)3 sass2,3- AZUL(CFs). {3,5,7- AZUL(CF4 2,3,5- AZUL(CF3)4 8,2,3,6- 4-3 AZUL(CFs). 8: 7 AZL- CSHF is 2,3,5,7- 5- AZUL(CFs): Figure 21 U.S. Patent Feb. 2, 2016 Sheet 21 of 22 US 9.249,071 B2 PHENANTHRENE(CFs). i Molecular Name Structure formula By: 1 PHEN-5-1 C19HsF15 1,3,6,7,9- X-ray FC PHEN(CF3)s ( ) CF3 Fc-() ( ) FC CF3 PYRENE(CFs). hi Molecular Name Structure formula By: 1 PYRN-5-1 C21H5F15 1,3,4,6,8- X-ray CF PYRN(CFs). cuC “rer,CF CF 2 PYRN-5-2 C21H5F15 1,3,4,6,9- X-ray CF3 PYRN(CF).5 FC CCC.CF3 CF 3 PYRN-5-3 C21Hs F15 NMR 4.
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