Creation of persistent charge-transfer interactions in TCNQ polyester

Polymer Journal

Volumn 43, Issue 4, 2011, Pages 364-369

  Washino, Yusuke ^a   Murata, Kimie ^a   Ashizawa, Minoru ^a   Kawauchi, Susumu ^a   Michinobu, Tsuyoshi ^a,b  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

addition reaction; charge transfer; electrochemistry; post functionalization

Indexed keywords

CATHODIC DIRECTION; CHARGE TRANSFER INTERACTION; ELECTRON-RICH; ELEMENTAL ANALYSIS; FUNCTIONALIZATIONS; FUNCTIONALIZED POLYMERS; HIGH THERMAL STABILITY; LOW ENERGIES; NEAR-INFRARED; ONSET TEMPERATURE; OXIDATION POTENTIALS; POSITIVE SOLVATOCHROMISM; POST-FUNCTIONALIZATION; REDOX BEHAVIOR; REDUCTION POTENTIAL; SIDE REACTIONS; TETRACYANOQUINODIMETHANE;

ACETYLENE; CHARGE TRANSFER; CHROMOPHORES; ELECTROCHEMISTRY; FUNCTIONAL POLYMERS; ION EXCHANGE; MAGNETIC RESONANCE; MASS TRANSFER;

ADDITION REACTIONS;

EID: 79953706910     PISSN: 00323896     EISSN: 13490540     Source Type: Journal    
DOI: 10.1038/pj.2011.2     Document Type: Article

References (25)

1. Shirakawa, H., Louis, E. J., MacDiarmid, A. G., Chiang, C. K. & Heeger, A. J. Synthesis of electrically conducting organic polymers: halogen derivatives of polyacetylene, (CH)x. J. Chem. Soc. Chem. Commun 578-580 (1977).
2. Yamamoto, T., Morita, A., Miyazaki, Y., Maruyama, T., Wakayama, H., Zhou, Z.-h., Nakamura, Y. & Kanbara, T. Preparation of p-conjugated poly(thiophene-2,5-diyl), poly(p-phenylene), and related polymers using Zerovalent Nickel complexes. linear structure and properties of the p-conjugated polymers. Macromolecules 25, 1214-1223 (1992).
3. Michinobu, T., Inui, J. & Nishide, H. m-Phenylene-linked aromatic poly(aminium cationic radical)s: persistent high-spin organic polyradicals. Org. Lett. 5, 2165-2168 (2003). (Pubitemid 37140952)
4. Michinobu, T., Kato, F., Inui, J. & Nishide, H. Two-dimensionally extended aromatic polyamines for optimization of charge-transporting properties by partial oxidation. J. Polym. Sci.: Part A: Polym. Chem. 47, 4577-4586 (2009).
5. Michinobu, T., Inui, J. & Nishide, H. Two-dimensionally extended organic high-spin poly(aminium cationic radical)s and their magnetic force microscopic images. Polym. J. 42, 575-582 (2010).
6. Saito, S., Tsutsui, T., Tokito, S., Hara, T. & Chiu, H.- T. Electron transport in doped and undoped polymers containing p-conjugated groups. Polym. J. 17, 209-216 (1985). (Pubitemid 15540597)
7. Yoshioka, N., Nishide, H., Inagaki, K. & Tsuchida, E. Electrical conductive and magnetic properties of conjugated tetrathiolate nickel polymers. Polym. Bull. 23, 631-636 (1990). (Pubitemid 20710048)
8. Naka, K., Uemura, T. & Chujo, Y. Synthesis of p-conjugated poly(dithiafulvene) by cycloaddition polymerization of aldothioketene with Its alkynethiol tautomer. Macromolecules 31, 7570-7571 (1998). (Pubitemid 128563481)
9. Oyaizu, K., Mitsuhashi, F. & Tsuchida, E. Palladium-catalyzed synthesis of oligo(- methylthio)aniline and conversion to polyacene-type electrolytes bearing phonothiazinium repeating units. Macromol. Chem. Phys. 203, 1328-1336 (2002).
10. Inagi, S., Naka, K. & Chujo, Y. Functional polymers based on electron-donating TTF and derivatives. J. Mater. Chem. 17, 4122-4135 (2007). (Pubitemid 47512921)
11. Michinobu, T. Click synthesis of donor-acceptor type aromatic polymers. Pure Appl. Chem. 82, 1001-1009 (2010).
12. Kato, S.-i. & Diederich, F. Non-planar push-pull chromophores. Chem. Commun. 46, 1994-2006 (2010).
13. Michinobu, T. Click-type reaction of aromatic polyamines for improvement of thermal and optoelectronic properties. J. Am. Chem. Soc. 130, 14074-14075 (2008).
14. Li, Y. & Michinobu, T. Sequential double click reactions: a highly efficient post-functionalization method for optoelectronic polymers. Polym. Chem. 1, 72-74 (2010).
15. Li, Y., Tsuboi, K. & Michinobu, T. Double click synthesis and second-order nonlinearities of polystyrenes bearing donor-acceptor chromophores. Macromolecules 43, 5277-5286 (2010).
16. Li, Y., Tsuboi, K., Michinobu, T., Ishida, Y., Hirai, T., Hayakawa, T. & Kakimoto, M.-a. Efficient synthesis of block copolymers bearing donor-acceptor chromophores for second-order nonlinear optical applications. J. Photopolym. Sci. Technol. 23, 337-342 (2010).
17. Michinobu, T., Kumazawa, H., Noguchi, K. & Shigehara, K. One-step synthesis of donor-acceptor type conjugated polymers from ferrocene-containing poly(aryleneethynylene) s. Macromolecules 42, 5903-5905 (2009).
18. Wang, D. & Michinobu, T. One-step synthesis of ladder-type fused poly(benzopentalene) derivatives with tunable energy levels by variable substituents. J. Polym. Sci.: Part A: Polym. Chem. 49, 72-81 (2011).
19. Day, R. W., Inzelt, G., Kinstle, J. F. & Chambers, J. Q. Tetracyanoquinodimethanemodified electrodes. J. Am. Chem. Soc. 104, 6804-6805 (1982).
20. Kivala, M., Boudon, C., Gisselbrecht, J.- P., Seiler, P., Gross, M. & Diederich, F. A novel reaction of 7,7,8,8-tetracyanoquinodimethane (TCNQ): charge-transfer chromophores by [2+2] cycloaddition with alkynes. Chem. Commun. 4731-4733 (2007). (Pubitemid 350115386)
21. Michinobu, T., May, J. C., Lim, J. H., Boudon, C., Gisselbrecht, J.- P., Seiler, P., Gross, M., Biaggio, I. & Diederich, F. A new class of organic donor-acceptor molecules with large third-order optical nonlinearities. Chem. Commun 737-739 (2005). (Pubitemid 40313296)
22. Michinobu, T., Boudon, C., Gisselbrecht, J.- P., Seiler, P., Frank, B., Moonen, N. N. P., Gross, M. & Diederich, F. Donor-substituted 1,1,4,4-tetracyanobutadienes: new chromophores with efficient intramolecular charge-transfer interactions by atom-economic synthesis. Chem. Eur. J. 12, 1889-1905 (2006).
23. Kivala, M., Stanoeva, T., Michinobu, T., Frank, B., Gescheidt, G. & Diederich, F. Oneelectron reduced and oxidized stages of donor-substituted 1,1,4,4-tetracyanobuta-1,3- dienes of different molecular architectures. Chem. Eur. J. 14, 7638-7647 (2008).
24. Connelly, N. G. & Geiger, W. E. Chemical redox agents for organometallic chemistry. Chem. Rev. 96, 877-910 (1996). (Pubitemid 126649167)
25. Yuan, Y. & Michinobu, T. Energy level tuning of polythiophene derivative by click chemistry-type post-functionalization of side chain alkynes. J. Polym. Sci.: Part A: Polym. Chem. 49, 225-233 (2011).