Imidazole as a parent π-conjugated backbone in charge-transfer chromophores

. 2012 ; 8 () : 25-49. [epub] 20120105

Status PubMed-not-MEDLINE Jazyk angličtina Země Německo Médium print-electronic

Typ dokumentu časopisecké články

Perzistentní odkaz   https://www.medvik.cz/link/pmid22423270

Research activities in the field of imidazole-derived push-pull systems featuring intramolecular charge transfer (ICT) are reviewed. Design, synthetic pathways, linear and nonlinear optical properties, electrochemistry, structure-property relationships, and the prospective application of such D-π-A organic materials are described. This review focuses on Y-shaped imidazoles, bi- and diimidazoles, benzimidazoles, bis(benzimidazoles), imidazole-4,5-dicarbonitriles, and imidazole-derived chromophores chemically bound to a polymer chain.

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Forrest S R, Thompson M E, editors. Organic Electronics and Optoelectronics. Chem Rev. 2007;107:923–1386.

Miller R D, Chandross E A, editors. Materials for Electronics. Chem Rev. 2010;110:1–574. PubMed

He G S, Tan L-S, Zheng Q, Prasad P N. Chem Rev. 2008;108:1245–1330. doi: 10.1021/cr050054x. PubMed DOI

Kuzyk M G. J Mater Chem. 2009;19:7444–7465. doi: 10.1039/b907364g. DOI

Bureš F, Schweizer W B, May J C, Boudon C, Gisselbrecht J-P, Gross M, Biaggio I, Diederich F. Chem–Eur J. 2007;13:5378–5387. doi: 10.1002/chem.200601735. PubMed DOI

May J C, Biaggio I, Bureš F, Diederich F. Appl Phys Lett. 2007;90:251106. doi: 10.1063/1.2750396. DOI

Bureš F, Pytela O, Kivala M, Diederich F. J Phys Org Chem. 2011;24:274–281. doi: 10.1002/poc.1744. DOI

Debus H. Justus Liebigs Ann Chem. 1858;107:199–208. doi: 10.1002/jlac.18581070209. DOI

Radziszewski B. Ber Dtsch Chem Ges. 1882;15:2706–2708. doi: 10.1002/cber.188201502245. DOI

Grimmett M R. Imidazole and Benzimidazole Synthesis. San Diego: Academic Press; 1997.

Patel A, Bureš F, Ludwig M, Kulhánek J, Pytela O, Růžička A. Heterocycles. 2009;78:999–1013. doi: 10.3987/COM-08-11609. DOI

Kulhánek J, Bureš F, Mikysek T, Ludvík J, Pytela O. Dyes Pigm. 2011;90:48–55. doi: 10.1016/j.dyepig.2010.11.004. DOI

Wang S, Zhao L, Xu Z, Wu C, Cheng S. Mater Lett. 2002;56:1035–1038. doi: 10.1016/S0167-577X(02)00671-7. DOI

Bu X R, Li H, Van Derveer D, Mintz E A. Tetrahedron Lett. 1996;37:7331–7334. doi: 10.1016/0040-4039(96)01638-3. DOI

Ren J, Wang S-M, Wu L-F, Xu Z-X, Dong B-H. Dyes Pigm. 2008;76:310–314. doi: 10.1016/j.dyepig.2006.09.003. DOI

Wu W, Ye C, Wang D. ARKIVOC. 2003;ii:59–69.

Wu W, Zhang Z, Zhang X. J Nonlinear Opt Phys Mater. 2005;14:61–65. doi: 10.1142/S0218863505002499. DOI

Yang Z, Qin A, Zhang S, Ye C. Eur Polym J. 2004;40:1981–1986. doi: 10.1016/j.eurpolymj.2004.04.012. DOI

Dierschke F, Müllen K. Macromol Chem Phys. 2007;208:37–43. doi: 10.1002/macp.200600412. DOI

Kulhánek J, Bureš F, Pytela O, Mikysek T, Ludvík J. Chem–Asian J. 2011;6:1604–1612. doi: 10.1002/asia.201100097. PubMed DOI

Wright J B. Chem Rev. 1951;48:397–541. doi: 10.1021/cr60151a002. PubMed DOI

Preston P N. Chem Rev. 1974;74:279–314. doi: 10.1021/cr60289a001. DOI

Batista R M F, Costa S P G, Belsey M, Lodeiro C, Raposo M M M. Tetrahedron. 2008;64:9230–9238. doi: 10.1016/j.tet.2008.07.043. DOI

Batista R M F, Costa S P G, Belsey M, Raposo M M M. Tetrahedron. 2007;63:9842–9849. doi: 10.1016/j.tet.2007.06.098. DOI

Carella A, Centore R, Fort A, Peluso A, Sirigu A, Tuzi A. Eur J Org Chem. 2004:2620–2626. doi: 10.1002/ejoc.200300786. DOI

Yang D, Fokas D, Li J, Yu L, Baldino C M. Synthesis. 2005:47–56. doi: 10.1055/s-2004-834926. DOI

Woodward D W, inventor. 4,5-Imidazoledicarbonitrile and Method of Preparation. 2,534,331. U.S. Patent. 1950 Dec 19;

O’Connell J F, Parquette J, Yelle W E, Wang W, Rapoport H. Synthesis. 1988:767–771. doi: 10.1055/s-1988-27702. DOI

Johnson D M, Rasmussen P G. Macromolecules. 2000;33:8597–8603. doi: 10.1021/ma000779x. DOI

Kulhánek J, Bureš F, Pytela O, Mikysek T, Ludvík J, Růžička A. Dyes Pigm. 2010;85:57–65. doi: 10.1016/j.dyepig.2009.10.004. DOI

Moylan C R, Miller R D, Twieg R J, Betterton K M, Lee V Y, Matray T J, Nguyen C. Chem Mater. 1993;5:1499–1508. doi: 10.1021/cm00034a021. DOI

Miller R D, Lee V Y, Moylan C R. Chem Mater. 1994;6:1023–1032. doi: 10.1021/cm00043a026. DOI

Santos J, Mintz E A, Zehnder O, Bosshard C, Bu X R, Günter P. Tetrahedron Lett. 2001;42:805–808. doi: 10.1016/S0040-4039(00)02143-2. DOI

Bu X R, VanDerveer D, Santos J, Hsu F-L, Wang J, Bota K. Anal Sci. 2003;19:469–470. doi: 10.2116/analsci.19.469. PubMed DOI

Feng K, De Boni L, Misoguti L, Mendonça C R, Meador M, Hsu F-L, Bu X R. Chem Commun. 2004:1178–1180. doi: 10.1039/b402019g. PubMed DOI

Feng K, Hsu F-L, VanDerveer D, Bota K, Bu X R. J Photochem Photobiol, A. 2004;165:223–228. doi: 10.1016/j.jphotochem.2004.03.021. DOI

Fang Z, Wang S, Zhao L, Xu Z, Ren J, Wang X, Yang Q. Mater Lett. 2007;61:4803–4806. doi: 10.1016/j.matlet.2007.03.038. DOI

Yan Y-X, Sun Y-H, Tian L, Fan H-H, Wang H-Z, Wang C-K, Tian Y-P, Tao X-T, Jiang M-H. Opt Mater. 2007;30:423–426. doi: 10.1016/j.optmat.2006.11.073. DOI

Yan Y-X, Fan H-H, Lam C-K, Huang H, Wang J, Hu S, Wang H-Z, Chen X-M. Bull Chem Soc Jpn. 2006;79:1614–1619. doi: 10.1246/bcsj.79.1614. DOI

Zhang M, Li M, Zhao Q, Li F, Zhang D, Zhang J, Yi T, Huang C. Tetrahedron Lett. 2007;48:2329–2333. doi: 10.1016/j.tetlet.2007.01.158. DOI

Velusamy M, Hsu Y-C, Lin J T, Chang C-W, Hsu C-P. Chem–Asian J. 2010;5:87–96. doi: 10.1002/asia.200900244. PubMed DOI

Xu Z-X, Wang S-M, Zhao L, Zhang S-L, Li J-B. Chin J Org Chem. 2003;23:950–952.

Zhao L, Wang S-M, Xu Z-X, Zhang S-L, Wu C-H, Cheng S-Y. Chem Res Chin Univ. 2003;19:28–31.

Chuang W-T, Chen B-S, Chen K-Y, Hsieh C-C, Chou P-T. Chem Commun. 2009:6982–6984. doi: 10.1039/b908542d. PubMed DOI

Jayabharathi J, Thanikachalam V, Srinivasan N, Saravanan K. J Fluoresc. 2011;21:595–606. doi: 10.1007/s10895-010-0747-5. PubMed DOI

Sekar N. Colourage. 2002;49:59–60.

Wu W, Zhang Z, Zhang X. J Chem Res. 2004:617–619. doi: 10.3184/0308234042430548. DOI

Ra C S, Kim S C, Park G. J Mol Struct: THEOCHEM. 2004;677:173–178. doi: 10.1016/j.theochem.2004.01.025. DOI

Jug K, Chiodo S, Calaminici P, Avramopoulos A, Papadopoulos M G. J Phys Chem A. 2003;107:4172–4183. doi: 10.1021/jp022403m. DOI

Li S, Yang Z, Wang P, Kang H, Wu W, Ye C, Yang M, Yang X. Macromolecules. 2002;35:4314–4316. doi: 10.1021/ma011598d. DOI

Yang Z, Li S, Ye C. J Polym Sci, Part A: Polym Chem. 2002;40:4297–4301. doi: 10.1002/pola.10505. DOI

Li S, Yang Z, Ye C. Chin J Polym Sci. 2004;22:453–457.

Li S, Kang H, Wu W, Ye C. J Appl Polym Sci. 2008;110:3758–3762. doi: 10.1002/app.23405. DOI

Zhao L, Li S B, Wen G A, Peng B, Huang W. Mater Chem Phys. 2006;100:460–463. doi: 10.1016/j.matchemphys.2006.01.025. DOI

Fridman N, Kaftory M, Speiser S. Sens Actuators, B. 2007;126:107–115. doi: 10.1016/j.snb.2006.10.066. DOI

Pina J, Seixas de Melo J S, Batista R M F, Costa S P G, Raposo M M M. J Phys Chem B. 2010;114:4964–4972. doi: 10.1021/jp9104954. PubMed DOI

Li Z, Lin Y, Xia J-L, Zhang H, Fan F, Zeng Q, Feng D, Yin J, Liu S H. Dyes Pigm. 2011;90:245–252. doi: 10.1016/j.dyepig.2010.09.015. DOI

Yuan J, Li Z, Hu M, Li S, Huang S, Yin J, Liu S H. Photochem Photobiol Sci. 2011;10:587–591. doi: 10.1039/c0pp00337a. PubMed DOI

Sakaino Y, Kakisawa H, Kusumi T, Maeda K. J Org Chem. 1979;44:1241–1244. doi: 10.1021/jo01322a010. DOI

Gompper R, Mehrer M, Polborn K. Tetrahedron Lett. 1993;34:6379–6382. doi: 10.1016/0040-4039(93)85050-7. DOI

Wang P, Zhu P, Wu W, Kang H, Ye C. Phys Chem Chem Phys. 1999;1:3519–3525. doi: 10.1039/a903535d. DOI

Carella A, Casalboni M, Centore R, Fusco S, Noce C, Quatela A, Peluso A, Sirigu A. Opt Mater. 2007;30:473–477. doi: 10.1016/j.optmat.2006.12.006. DOI

Carella A, Centore R, Mager L, Barsella A, Fort A. Org Electron. 2007;8:57–62. doi: 10.1016/j.orgel.2006.10.008. DOI

Yu J, Cui Y, Gao J, Wang Z, Qian G. J Phys Chem B. 2009;113:14877–14883. doi: 10.1021/jp9048549. PubMed DOI

Cross E M, White K M, Moshrefzadeh R S, Francis C V. Macromolecules. 1995;28:2526–2532. doi: 10.1021/ma00111a055. DOI

Cross E M, Francis C V, inventors. Benzimidazole-Derivatized Azo Compounds and Polymers Derived Therefrom for Nonlinear Optics. 5,321,084. U.S. Patent. 1994 Jun 14;

Batista R M F, Costa S P G, Belsley M, Raposo M M M. Dyes Pigm. 2009;80:329–336. doi: 10.1016/j.dyepig.2008.08.001. DOI

Sun Y-F, Huang W, Lu C-G, Cui Y-P. Dyes Pigm. 2009;81:10–17. doi: 10.1016/j.dyepig.2008.08.003. DOI

Guo J-G, Cui Y-M, Lin H-X, Xie X-Z, Chen H-F. J Photochem Photobiol, A. 2011;219:42–49. doi: 10.1016/j.jphotochem.2011.01.014. DOI

Eseola A O, Li W, Sun W-H, Zhang M, Xiao L, Woods J A O. Dyes Pigm. 2011;88:262–273. doi: 10.1016/j.dyepig.2010.07.005. DOI

Wu J, Liu S-X, Neels A, Le Derf F, Sallé M, Decurtins S. Tetrahedron. 2007;63:11282–11286. doi: 10.1016/j.tet.2007.08.091. DOI

Sanguinet L, Pozzo J-L, Guillaume M, Champagne B, Castet F, Ducasse L, Maury E, Soulié J, Mançois F, Adamietz F, et al. J Phys Chem B. 2006;110:10672–10682. doi: 10.1021/jp060825g. PubMed DOI

Rodembusch F S, Buckup T, Segala M, Tavares L, Correia R R B, Stefani V. Chem Phys. 2004;305:115–121. doi: 10.1016/j.chemphys.2004.06.046. DOI

Douhal A, Armat-Guerri F, Lillo M P, Acuña A U. J Photochem Photobiol, A. 1994;78:127–138. doi: 10.1016/1010-6030(93)03724-U. DOI

Barashkov N N, Novikova T S, Guerrero D J, Ferraris J P. Synth Met. 1995;75:241–248. doi: 10.1016/0379-6779(96)80014-2. DOI

Zhang X-H, Kim S-H, Lee I-S, Gao C-J, Yang S-I, Ahn K-H. Bull Korean Chem Soc. 2007;28:1389–1395. doi: 10.5012/bkcs.2007.28.8.1389. DOI

Saito R, Matsumura Y, Suzuki S, Okazaki N. Tetrahedron. 2010;66:8273–8279. doi: 10.1016/j.tet.2010.08.036. DOI

Luo Z, Shi H, Zhu H, Song G, Liu Y. Dyes Pigm. 2012;92:596–602. doi: 10.1016/j.dyepig.2011.06.030. DOI

Abe J, Shirai Y, Nemoto N, Nagase Y. J Phys Chem B. 1997;101:1910–1915. doi: 10.1021/jp962157c. DOI

Muhammad S, Xu H, Janjua M R S A, Su Z, Nadeem M. Phys Chem Chem Phys. 2010;12:4791–4799. doi: 10.1039/b924241d. PubMed DOI

Densmore C G, Rasmussen P G. Macromolecules. 2004;37:5900–5910. doi: 10.1021/ma035920r. DOI

Apen P G, Rasmussen P G. Heterocycles. 1989;29:1325–1329. doi: 10.3987/COM-89-4980. DOI

Subrayan R P, Kampf J W, Rasmussen P G. J Org Chem. 1994;59:4341–4345. doi: 10.1021/jo00094a060. DOI

Subrayan R P, Rasmussen P G. Tetrahedron. 1995;51:6167–6178. doi: 10.1016/0040-4020(95)00284-F. DOI

Subrayan R P, Rasmussen P G. Tetrahedron. 1999;55:353–358. doi: 10.1016/S0040-4020(98)01058-8. DOI

Jang T, Rasmussen P G. J Polym Sci, Part A: Polym Chem. 1998;36:2619–2629. doi: 10.1002/(SICI)1099-0518(199810)36:14<2619::AID-POLA22>3.0.CO;2-K. DOI

Apen P G, Rasmussen P G. J Polym Sci, Part A: Polym Chem. 1992;30:203–210. doi: 10.1002/pola.1992.080300204. DOI

Jang T, Rasmussen P G. J Polym Sci, Part A: Polym Chem. 2000;38:3828–3838. doi: 10.1002/1099-0518(20001015)38:20<3828::AID-POLA140>3.0.CO;2-8. DOI

Rasmussen P G, Hough R L, Anderson J E, Bailey O H, Bayon J C. J Am Chem Soc. 1982;104:6155–6156. doi: 10.1021/ja00386a071. DOI

Allan D S, Bergstrom D F, Rasmussen P G. Synth Met. 1988;25:139–155. doi: 10.1016/0379-6779(88)90349-9. DOI

Apen P G, Rasmussen P G. J Am Chem Soc. 1991;113:6178–6187. doi: 10.1021/ja00016a038. DOI

Coad E C, Liu H, Rasmussen P G. Tetrahedron. 1999;55:2811–2826. doi: 10.1016/S0040-4020(99)00060-5. DOI

Coad E C, Apen P G, Rasmussen P G. J Am Chem Soc. 1994;116:391–392. doi: 10.1021/ja00080a053. DOI

Coad E C, Kampf J, Rasmussen P G. J Org Chem. 1996;61:6666–6672. doi: 10.1021/jo960828x. PubMed DOI

Rasmussen P G, Fabre T S, Beck P A, Eissa M J, Escobedo J, Strongin R M. Tetrahedron Lett. 2001;42:6823–6825. doi: 10.1016/S0040-4039(01)01430-7. DOI

Allan D S, Thurber E L, Rasmussen P G. J Polym Sci, Part A: Polym Chem. 1990;28:2475–2483. doi: 10.1002/pola.1990.080280920. DOI

Thurber E L, Rasmussen P G. J Polym Sci, Part A: Polym Chem. 1993;31:351–364. doi: 10.1002/pola.1993.080310207. DOI

Kim Y-K, Rasmussen P G. J Polym Sci, Part A: Polym Chem. 1993;31:2583–2594. doi: 10.1002/pola.1993.080311019. DOI

Bouck K J, Rasmussen P G. Macromolecules. 1993;26:2077–2084. doi: 10.1021/ma00060a041. DOI

Donald D S, Webster O W. Adv Heterocycl Chem. 1987;41:1–40. doi: 10.1016/S0065-2725(08)60159-2. DOI

Heckmeier M, Farrand L D, inventors. 4,5-Dicyanoimidazole Derivatives and Their Use in Liquid Crystal Media and Liquid Crystal Devices. GB 2 396 154 A. GB Patent Application. 2004 Jun 16;

Hardgrove G L, Jons S D. Acta Crystallogr. 1991;C47:337–339.

Carella A, Centore R, Sirigu A, Tuzi A, Quatela A, Schutzmann S, Casalboni M. Macromol Chem Phys. 2004;205:1948–1954. doi: 10.1002/macp.200400129. DOI

Carella A, Centore R, Riccio P, Sirigu A, Quatela A, Palazzesi C, Casalboni M. Macromol Chem Phys. 2005;206:1399–1404. doi: 10.1002/macp.200500112. DOI

Cui Y, Qian G, Chen L, Wang Z, Wang M. Macromol Rapid Commun. 2007;28:2019–2023. doi: 10.1002/marc.200700375. DOI

Yu J, Qiu J, Cui Y, Hu J, Liu L, Xu L, Qian G. Mater Lett. 2009;63:2594–2596. doi: 10.1016/j.matlet.2009.09.019. DOI

Kulhánek J, Bureš F, Ludwig M. Beilstein J Org Chem. 2009;5:No. 11. doi: 10.3762/bjoc.5.11. PubMed DOI PMC

Kulhánek J, Bureš F, Wojciechowski A, Makowska-Janusik M, Gondek E, Kityk I V. J Phys Chem A. 2010;114:9440–9446. doi: 10.1021/jp1047634. PubMed DOI

Plaquet A, Champagne B, Kulhánek J, Bureš F, Bogdan E, Castet F, Ducasse L, Rodriguez V. ChemPhysChem. 2011;12:3245–3252. doi: 10.1002/cphc.201100299. PubMed DOI

Nepraš M, Almonasy N, Bureš F, Kulhánek J, Dvořák M, Michl M. Dyes Pigm. 2011;91:466–473. doi: 10.1016/j.dyepig.2011.03.025. DOI

Danko M, Hrdlovič P, Kulhánek J, Bureš F. J Fluoresc. 2011;21:1779–1787. doi: 10.1007/s10895-011-0872-9. PubMed DOI

Bureš F, Kulhánek J, Mikysek T, Ludvík J, Lokaj J. Tetrahedron Lett. 2010;51:2055–2058. doi: 10.1016/j.tetlet.2010.02.067. DOI

Lokaj J, Moncol J, Bureš F, Kulhánek J. J Chem Crystallogr. 2011;41:834–837. doi: 10.1007/s10870-011-0007-9. DOI

Ma L P, Liu J, Yang Y. Appl Phys Lett. 2002;80:2997–2999. doi: 10.1063/1.1473234. DOI

Shin R Y C, Kietzke T, Sudhakar S, Dodabalapur A, Chen Z-K, Sellinger A. Chem Mater. 2007;19:1892–1894. doi: 10.1021/cm070144d. DOI

Shin R Y C, Sonar P, Siew P S, Chen Z-K, Sellinger A. J Org Chem. 2009;74:3293–3298. doi: 10.1021/jo802720m. PubMed DOI

Kietzke T, Shin R Y C, Egbe D A M, Chen Z-K, Sellinger A. Macromolecules. 2007;40:4424–4428. doi: 10.1021/ma0706273. DOI

Ooi Z E, Tam T L, Shin R Y C, Chen Z-K, Kietzke T, Sellinger A, Baumgarten M, Mullen K, deMello J C. J Mater Chem. 2008;18:4619–4622. doi: 10.1039/b813786m. DOI

Zeng W, Chong K S L, Low H Y, Williams E L, Tam T L, Sellinger A. Thin Solid Films. 2009;517:6833–6836. doi: 10.1016/j.tsf.2009.05.024. DOI

Schubert M, Yin C, Castellani M, Bange S, Tam T L, Sellinger A, Hörhold H-H, Kietzke T, Neher D. J Chem Phys. 2009;130:094703. doi: 10.1063/1.3077007. PubMed DOI

Lindsay G A. Second-Order Nonlinear Optical Polymers. In: Lindsay G A, Singer K D, editors. Polymers for Second-Order Nonlinear Optics. Washington, DC: American Chemical Society; 1995. pp. 1–19. DOI

Wu W, Wang D, Ye C. Polym Bull. 1998;41:401–408. doi: 10.1007/s002890050380. DOI

Zhu P, Wang P, Wu W, Ye C J. Nonlinear Opt Phys Mater. 1999;8:461–468. doi: 10.1142/S0218863599000333. DOI

Kang H, Wu W, Wu P, Ye C. Chin Sci Bull. 2001;46:827–830. doi: 10.1007/BF02900432. DOI

Pan Y, Tang X, Zhu L, Huang Y. Eur Polym J. 2007;43:1091–1095. doi: 10.1016/j.eurpolymj.2006.12.010. DOI

Pan Y, Tang X. J Appl Polym Sci. 2008;108:2802–2807. doi: 10.1002/app.27579. DOI

Pan Y, Tang X. Synth Met. 2009;159:1796–1799. doi: 10.1016/j.synthmet.2009.05.027. DOI

Koszykowska M, Tokarek M, Kucharski S. Mater Sci Poland. 2009;27:699–708.

Lebedeva G K, Loretsyan N L, Ivanova V N, Romashkova K A, Lukoshkin V A, Kudryavtsev V V. Phys Solid State. 2002;44:395–398. doi: 10.1134/1.1451035. DOI

Wang X, Yang K, Kumar J, Tripathy S K, Chittibabu K G, Li L, Lindsay G. Macromolecules. 1998;31:4126–4134. doi: 10.1021/ma971615s. DOI

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