Low bandgap conducting polymers

Conjugated Polymers: Theory, Synthesis, Properties, and Characterization

Volumn 1, Issue , 2007, Pages 12-1-12-42

  Rasmussen, Seth C ^a   Pomerantz, Martin ^b  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

^b UNIVERSITY OF TEXAS AT ARLINGTON   (United States)

Author keywords

[No Author keywords available]

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EID: 84975725458     PISSN: None     EISSN: None     Source Type: Book    
DOI: None     Document Type: Chapter

References (183)

1. Pomerantz, M. 1998. Low band gap conducting polymers. Handbook of conducting polymers, 2nd ed., eds. T.A. Skotheim, R.L. Elsenbaumer, and J.R. Reynolds. New York: Marcel Dekker, chap. 11, p. 277
2. Groenendaal, L., et al. 2000. Poly(3,4-ethylenedioxythiophene) and its derivatives: Past, present, and future. Adv Mater 12:481.
3. Wudl, F., M. Kobayashi, and A.J. Heeger. 1984. Poly(isothianaphthene). J Org Chem 49:3382.
4. Kobayashi, M., et al. 1985. The electronic and electrochemical properties of poly(isothianaphthene). J Chem Phys 82:5717.
5. McCullough, R.D. and P.C. Ewbank. 1998. Regioregular, head-to-tail coupled poly(3-alkylthiophene) and its derivatives. Handbook of conducting polymers, 2nd ed., eds. T.A. Skotheim, R.L. Elsenbaumer, and J.R. Reynolds. New York: Marcel Dekker, chap. 9, p.225
6. Roncali, J. 1997. Synthetic principles for bandgap control in linear p-conjugated systems. Chem Rev 97:173.
7. Chan, H.S.O. and S. Ng. 1998. Synthesis, characterization and applications of thiophene-based functional polymers. Prog Polym Sci 23:1167.
8. Bakhshi, A.K. and P. Rattan. 1997. Electrically conducting polymers: An emerging technology. Curr Sci 73:648.
9. Bakhshi, A.K. and G. Bhalla. 2004. Electrically conducting polymers: Materials of the twenty-first century. J Sci Ind Res 63:715.
10. Bakhshi, A.K. and S. Kaul. 2001. Strategies for molecular designing of novel low-band-gap electrically conducting polymers. Appl Biochem Biotechnol 96:125.
11. Dietz, F., et al. 1994. Band structure of quasi-1-dimensional polycondensed p-systems, 3. Macromol Theory Simul 3:241.
12. Brocks, G. and E.E. Havinga. 2001. Small band gap polymers based upon anti-aromatic monomers. Synth Met 119:93.
13. Kertesz, M., C.H. Choi, and G. Sun. 1998. Design strategies for small bandgap conjugated polymers. Polym Prepr (Am Chem Soc Div Polym Chem) 39(1):76.
14. Hutchison, G.R., M.A. Ratner, and T.J. Marks. 2005. Electronic structure and band gaps in cationic heterocyclic oligomers, multidimensional analysis of the interplay of heteroatoms, substituents, molecular length, and charge on redox and transparency characteristics. J Phys Chem B 109:3126.
15. Kwon, O. and M.L. McKee. 2000. Theoretical calculations of band gaps in the aromatic structures of polythieno[3,4-b]benzene and polythieno[3,4-b]pyrazine. J Phys Chem A 104:7106.
16. Pomerantz, M., et al. 1992. Poly(2,3-dihexylthieno[3,4-b]pyrazine). A new processable low bandgap polyheterocycle. J Chem Soc Chem Commun 1672.
17. Pomerantz, M., et al. 1993. New processable low band-gap, conjugated polyheterocycles. Synth Met 55:960.
18. Toussaint, J.M. and J.L. Brédas. 1995. Geometric and electronic structure of polydicyanomethylene- cyclopenta-dicyclopentadiene, a conjugated polymer possessing a very small intrinsic bandgap. Synth Met 69:637.
19. Bakhshi, A.K., Deepika and J. Ladik. 1997. Ab initio study of the electronic structures of polycyclopentadithiophene-4-one and polydicyanomethylene-cyclopentadithiophene: Two conjugated polymers with small band gaps. Solid State Commun 101:347.
20. Bakhshi, A.K., et al. 1996. Design of novel donor–acceptor polymers with low bandgaps. Synth Met 79:115.
21. Bakhshi, A.K. and P. Rattan. 1998. Ab initio study of novel low-band-gap donor–acceptor polymers based on poly(cyclopentadienylene). J Chem Soc Faraday Trans 94:2823.
22. Bakhshi, A.K. and G. Gandhi. 2004. Ab initio study of the electronic structures and conduction properties of some novel low band-gap donor–acceptor polymers. Solid State Commun 129:335.
23. Ferraris, J.P. and T.L. Lambert. 1991. Narrow bandgap polymers: Poly-4-dicyanomethylene-4Hcyclopenta[2,1-b;3,4-b]dithiophene (PCDM). J Chem Soc Chem Commun 1268.
24. Lambert, T.L. and J.P. Ferraris. 1991. Narrow band gap polymers: Polycyclopenta[2,1-b;3,4- b]dithiophen-4-one. J Chem Soc Chem Commun 752.
25. Bakhshi, A.K., et al. 1998. Theoretical design of donor–acceptor polymers with low bandgaps. J Mol Struct 427:211.
26. Bakhshi, A.K. and P. Bhargava. 2003. Ab initio study of the electronic structures and conduction properties of some donor–acceptor polymers and their copolymers. J Chem Phys 119:13159.
27. Hong, S.Y. and K.W. Lee. 2000. Small band-gap polymers: Quantum-chemical study of electronic structures of degenerate p-conjugated systems. Chem Mater 12:155.
28. Hong, S.Y. and S.C. Kim. 2003. Towards designing environmentally stable conjugated polymers with very small band-gaps. Bull Korean Chem Soc 24:1649.
29. Hong, S.Y. 2000. Zero band-gap polymers: Quantum-chemical study of electronic structures of degenerate p-conjugated systems. Chem Mater 12:495.
30. Brocks, G. 1995. Ab initio electronic structure of a small band gap polymer: Poly-aminosquaraine. J Chem Phys 102:2522.
31. Brocks, G. and A. Tol. 1996. Small band gap semiconducting polymers made from dye molecules: Polysquaraines. J Phys Chem 100:1838.
32. Duan, X., D.S. Dudis, and A.T. Yeates. 2001. Electronic structure and energy band gap studies for poly(1,3-thienyl-squaraine) and its dianion. Synth Met 116:285.
33. van Asselt, R., et al. 1995. New synthetic routes to poly(isothianaphthene). I. Reaction of phthalic anhydride and phthalide with phosphorus pentasulfide. Synth Met 74:65.
34. van Asselt, R., et al. 1996. New synthetic routes to poly(isothianaphthene). II. Mechanistic aspects of the reactions of phthalic anhydride and phthalide with phosphorus pentasulfide. J Polym Sci Part A: Polym Chem 34:1553.
35. Jen, K.-Y. and R. Elsenbaumer. 1986. Facile preparation of electrically conductive poly(isothianaphthene). Synth Met 16:379.
36. Paulussen, H., et al. 2001. New mechanistic aspects on the formation of poly(isothianaphthene) from P4S10 and phthalic anhydride derivatives: Carbon–carbon bone formation and cleavage via a cyclic reaction mechanism. Polymer 41:3121.
37. Paulussen, H., et al. 1997. Synthesis of poly(isothianapththene) from 1,1,3,3-tetrachlorothiophthalan and tert-butylmercaptan: Mechanism and quantitative analysis by solid state NMR. Polymer 38:5221.
38. Chen, S.-A. and C.-C. Lee. 1995. Conversion of poly(1,3-dihydroisothianaphthene) into polyisothianaphthene with the new dehydrogenation agent, tert-butyl hypochlorite. Synth Met 75:187.
39. Chen, S.-A. and C.-C. Lee. 1995. Processable low band gap p-conjugated polymer, poly(isothianaphthene): Its synthesis and reaction mechanism. Pure Appl Chem 67:1983.
40. Chen, S.-A. and C.-C. Lee. 1996. Processable low band gap p-conjugated polymer, poly(isothianaphthene). Polymer 37:519.
41. Chen, W.-T., et al. 2002. Modified synthetic routes to poly(isothianaphthene). Synth Met 128:215.
42. Chen, W.-T., G.A. Bowmaker, and R.P. Cooney. 2002. An electron paramagnetic resonance study of poly(isothianaphthene). Phys Chem Chem Phys 4:4218.
43. King, G. and S.J. Higgins. 1995. Synthesis and characterisation of novel substituted benzo[c]thiophenes and polybenzo[c]thiophenes: Tuning the potentials for n- and p-doping in transparent conducting polymers. J Mater Chem 5:447.
44. Burbridge, S.J., et al. 1994. Nonlinear optical properties of a soluble form of polyisothianaphthene. J Mod Opt 41:1217.
45. Burbridge, S.J., et al. 1995. The third order nonlinear optical response of a soluble form of polyisothianaphthene. Mol Cryst Liq Cryst Sci Technol Sect B Nonlin Opt 10:139.
46. Paulussen, H., D. Vanderzande, and J. Gelan. 1997. The synthesis and characterization of soluble poly(isothianaphthene)-derivatives. Synth Met 84:415.
47. Ottenbourgs, B., et al. 1997. Characterization of poly(isothianaphthene) derivatives and analogs by using solid-state 13C NMR. Synth Met 89:95.
48. Hagan, A.J., S.C. Moratti, and I.C. Sage. 2001. Synthesis of low band gap polymers: Studies in polyisothianaphthene. Synth Met 119:147.
49. Polec, I., et al. 2003. Convenient synthesis and polymerization of 5,6-disubstituted dithiophthalides toward soluble poly(isothianaphthene): An initial spectroscopic characterization of the resulting low-band-gap polymers. J Polym Sci Part A Polym Chem 41:1034.
50. Goris, L., et al. 2003. Poly(5,6-dithiooctylisothianaphthene), a new low band gap polymer: Spectroscopy and solar cell construction. Synth Met 138:249.
51. Swann, M.J., et al. 1993. Spectroscopic studies of the novel conducting polymer polytetrafluorobenzo- c-thiophene. Synth Met 55:281.
52. Kiebooms, R., et al. 1996. Poly(tetrafluorobenzo[c]thiophene). Structure analysis of oligomers and model compound based on 1D and 2D NMR spectroscopy. Macromolecules 29:5981.
53. Kiebooms, R., et al. 1997. Spectroscopic analysis of poly(tetrafluoroisothianaphthene) and aromatic model compounds. Synth Met 84:189.
54. Jones, C.L., S.J. Higgins, and P.A. Christensen. 2002. Some in situ reflectance fourier transform infrared studies of electrochemically prepared polybenzo[c]thiophene and poly-5-fluorobenzo[c]thiophene films. J Mater Chem 12:758.
55. Meng, H. and F. Wudl. 2001. A robust low band gap processable n-type conducting polymer based on poly(isothianaphthene). Macromolecules 34:1810.
56. Kastner, J., et al. 1995. Raman spectra and ground state of the new low bandgap polymer poly(thienopyrazine). Synth Met 69:593.
57. Kastner, J., et al. 1995. Raman spectra of poly(2,3-R, R-thieno[3,4-b]pyrazine). A new low-bandgap polymer. Macromolecules 28:2922.
58. Huskic, M., D. Vanderzande, and J. Gelan. 1999. Synthesis of aza-analogues of poly(isothianaphthene). Synth Met 99:143.
59. Kenning, D.D. and S.C. Rasmussen. 2003. A second look at polythieno[3,4-b]pyrazines: Chemical vs. electrochemical polymerization and its effect on band gap. Macromolecules 36:6298.
60. Nayak, K. and D.S. Marynick. 1990. The interplay between geometric and electronic structures in polyisothianaphthene, polyisonaphthothiophene, polythieno(3,4-b)pyrazine, and polythieno(3,4-b)quinoxaline. Macromolecules 23:2237.
61. Kenning, D.D., et al. 2002. Thieno[3,4-b]pyrazines: Synthesis, structure, and reactivity. J Org Chem 67:9073.
62. Kenning, D.D. and S.C. Rasmussen. Unpublished results.
63. Lorcy, D. and M.P. Cava. 1992. Poly(isothianaphthene-bithiophene): A new regularly structured polythiophene analog. Adv Mater 4:562.
64. Bäuerle, P., et al. 1992. Synthesis and characterization of new annulated terheterocycles. Adv Mater 4:564.
65. Hoogmartens, I., et al. 1992. An investigation into the electronic structure of poly(isothianaphthene). Synth Met 51:219.
66. Musmanni, S. and J.P. Ferraris. 1993. Preparation and characterization of conducting polymers based on 1,3-di(2-thienyl)benzo[c]thiophene. J Chem Soc Chem Commun 172.
67. Staes, E., et al. 1999. Properties of a low band gap conducting polymer electrode used for amperometric detection in liquid chromatography. Electroanalysis 11:65.
68. Vangeneugden, D., et al. 1998. Formal copolymers based on 1,3-dithienylisothianaphthene derivatives: Promising materials for electronic devices. Acta Polym 49:687.
69. Vangeneugden, D.L., et al. 1999. A general synthetic route towards soluble poly(1,3-dithienylisothianaphthene) derivatives. Synth Met 101:120.
70. Shaheen, S.E., et al. 2001. Low band-gap polymeric photovoltaic devices. Synth Met 121:1583.
71. Gebeyehu, D., et al. 2002. Hybrid solar cells based on dye-sensitized nanoporous TiO2 electrodes and conjugated polymers as hole transport materials. Synth Met 125:279.
72. Sonmez, G., H. Meng, and F. Wudl. 2003. Very stable low band gap polymer for charge storage purposes and near-infrared applications. Chem Mater 15:4923.
73. Meng, H., et al. 2003. An unusual electrochromic device based on a new low-bandgap conjugated polymer. Adv Mater 15:146.
74. Cravino, A., et al. 2003. Spectroscopic properties of PEDOTEHIITN, a novel soluble low band-gap conjugated polymer. Synth Met 137:1435.
75. Kitamura, C., S. Tanaka, and Y. Yamashita. 1994. Synthesis of new narrow bandgap polymers based on 5,7-di(2-thienyl)thieno[3,4-b]pyrazine and its derivatives. J Chem Soc Chem Commun 1585.
76. Kitamura, C., S. Tanaka, and Y. Yamashita. 1996. Design of narrow-bandgap polymers. Syntheses and properties of monomers and polymers containing aromatic-donor and o-quinoid-acceptor units. Chem Mater 8:570.
77. Sonmez, G., et al. 2004. A red, green, and blue (RGB) polymeric electrochromic device (PECD): The dawning of the PECD era. Angew Chem Int Ed 43:1498.
78. Sonmez, G., et al. 2005. A processable green polymeric electrochromic. Macromolecules 38:669.
79. Sonmez, G., et al. 2004. Red, green, and blue colors in polymeric electrochromics. Adv Mater 16:1905.
80. Berlin, A., et al. 2004. New low-gap polymers from 3,4-ethylenedioxythiophene-bis-substituted electron-poor thiophenes. The roles of thiophene, donor–acceptor alternation, and copolymerization in intrinsic conductivity. Chem Mater 16:3667.
81. Akoudad, S. and J. Roncali. 1998. Electrogenerated poly(thiophenes) with extremely narrow bandgap and high stability under n-doping cycling. Chem Commun 2081.
82. Akoudad, S. and J. Roncali. 1999. Electrogenerated poly(thiophenes) with extremely low bandgap. Synth Met 101:149.
83. Perepichka, I.F., E. Levillain, and J. Roncali. 2004. Effect of substitution of 3,4-ethylenedioxythiophene (EDOT) on the electronic properties of the derived electrogenerated low band gap conjugated polymers. J Mater Chem 14:1679.
84. Tanaka, S. and Y. Yamashita. 1995. Syntheses of narrow band gap heterocyclic copolymers of aromatic-donor and quinonoid-acceptor units. Synth Met 69:599.
85. Tanaka, S. and Y. Yamashita. 1997. A novel monomer candidate for intrinsically conductive organic polymers based on nonclassical thiophene. Synth Met 84:229.
86. Tachibana, M., et al. 2002. Small band-gap polymers involving tricyclic nonclassical thiophene as a building block. J Phys Chem B 106:3549.
87. Sonmez, G., et al. 2005. The unusual effect of bandgap lowering by C60 on a conjugated polymer. Adv Mater 17:897.
88. Zhang, F., et al. 2005. Polymer solar cells based on a low-bandgap fluorene copolymer and a fullerene derivative with photocurrent extended to 850 nm. Adv Funct Mater 15:745.
89. Krajcovic, J., et al. 1999. Synthesis of the copolymer of 2,3-di(1-tridecyl)thieno[3,4-b]pyrazine with 3-dodecylthiophene using the chemical oxidation with iron trichloride. Synth Met 105:79.
90. Cik, G., et al. 2001. Characterization and properties of the copolymer of dipyrido-[3,2-a;20,30-c]- thien-[3,4-c]azine with 3-dodecylthiophene. Synth Met 118:111.
91. Bolognesi, A., et al. 1988. Poly(dithieno[3,4-b:30,40-d]thiophene): A new transparent conducting polymer. J Chem Soc Chem Commun 246.
92. Taliani, C., et al. 1989. Optical properties of a low energy gap conduction polymer: Polydithieno[3,4-b:30,40-d]thiophene. Synth Met 28:C507.
93. Bolognesi, A., et al. 1989. Preparation and properties of a new conducting polyheterocycle: Polydithieno[3,4-b:30,40-d]thiophene (PDDT). Synth Met 28:C527.
94. Arbizzani, C., et al. 1995. N- and p-doped polydithieno[3,4-b:30,40-d]thiophene: A narrow band gap polymer for redox supercapacitors. Electrochim Acta 40:1871.
95. Arbizzani, C., et al. 1997. A spectroelectrochemical study of poly(dithienothiophenes). J Electroanal Chem 423:23.
96. Cravino, A., et al. 2000. Electrochemically- and photo-induced IR absorption of low band-gap polydithienothiophenes: A comparative study. Mater Res Soc Symp Proc 598:3.74.1.
97. Neugebauer, H., et al. 2003. Spectral signatures of positive and negative charged states in doped and photoexcited low band-gap polydithienothiophenes. Synth Met 139:747.
98. Neugebauer, H. 2004. Infrared signatures of postive and negative charge carriers in conjugated polymers with low band gaps. J Electroanal Chem 563:153.
99. Cravino, A., et al. 2002. Positive and negative charge carriers in doped or photoexcited polydithienothiophenes: A comparative study using Raman, infrared, and electron spin resonance spectroscopy. J Phys Chem B 106:3583.
100. Ehrenfreund, E., et al. 2004. Even parity states in small band gap p-conjugated polymers: Polydithienothiophenes. Chem Phys Lett 394:132.
101. Ehrenfreund, E., et al. 2005. Resonant Raman scattering dispersion in poly(dithieno[3,4-b:30,40-d]- thiophene): 2ag spectroscopy. Synth Met 150:251.
102. Inaoka, S. and D.M. Collard. 1997. Polymerization of substituted dithieno[3,4-b:30,40-d]thiophenes. Synth Met 84:193.
103. Inaoka, S. and D.M. Collard. 1999. Synthesis, polymerization, and characterization of substituted dithieno[3,4-b:30,40-d]thiophenes. J Mater Chem 9:1719.
104. Quattrocchi, C., et al. 1993. Electronic structure of polythieno[3,4-b;30,40-d]thiophene, a small bandgap conjugated polymer. Synth Met 55–57:4399.
105. Quattrocchi, C., et al. 1993. Theoretical investigation of the structure and electronic properties of poly(dithieno[3,4-b:30,40-d]thiophene), a small-band-gap conjugated polymer. Macromolecules 26:1260.
106. Arbizzani, C., et al. 1997. Polydithienothiophenes: Two new conjugated materials with narrow band gap. Synth Met 84:249.
107. Catellani, M., et al. 1999. Electronic structure of polydithienothiophene materials. Synth Met 101:175.
108. Cravino, A., et al. 2001. Vibrational spectroscopy on pDTT3—a low band gap polymer based on dithienothiophene. J Phys Chem B 105:46.
109. Pomerantz, M. and X. Gu. 1997. Poly(2-decylthieno[3,4-b]thiophene). A new soluble low-bandgap conducting polymer. Synth Met 84:243.
110. Pomerantz, M., X. Gu, and S.X. Zhang. 2001. Poly(2-decylthieno[3,4-b]thiophene-4,6-diyl). A new low band gap conducting polymer. Macromolecules 34:1817.
111. Neef, C.J., I.D. Brotherston, and J.P. Ferraris. 1999. Synthesis and electronic properties of poly (2-phenylthieno[3,4-b]thiophene): A new low band gap polymer. Chem Mater 11:1957.
112. Lee, K. and G.A. Sotzing. 2001. Poly(thieno[3,4-b]thiophene). A new stable low band gap conducting polymer. Macromolecules 34:5746.
113. Sotzing, G.A. and K. Lee. 2002. Poly(thieno[3,4-b]thiophene): A p- and n-dopable polythiophene exhibiting high optical transparency in the semiconducting state. Macromolecules 35:7281.
114. Lee, B., M.S. Yavuz, and G.A. Sotzing. 2005. Conjugated polymers from thieno[3,4-b]thiophene dimers. Polym Prepr (Am Chem Soc Div Polym Chem) 46:860.
115. Lee, B., and G.A. Sotzing. 2002. Aqueous phase polymerization of thieno[3,4-b]thiophene. Polym Prepr (Am Chem Soc Div Polym Chem) 43:568.
116. Sotzing, G.A., et al. 2003. Optically transparent conductive polymers from thieno[3,4-b]thiophene. Polym Mater Sci Eng 88:268.
117. Lee, B., V. Seshadri, and G.A. Sotzing. 2005. Suspension polymerization of thieno[3,4-b]thiophene in water to produce low band gap conjugated polymers. Polym Prepr (Am Chem Soc Div Polym Chem) 46:1010.
118. Lee, B., et al. 2005. Ring-sulfonated poly(thienothiophene) Adv Mater 17:1792.
119. Seshadri, V., et al. 2003. Conjugated polythiophene consisting of coupling through locked transoid conformation. Polym Mater Sci Eng 88:292.
120. Seshadri, V., L. Wu, and G.A. Sotzing. 2003. Conjugated polymers via electrochemical polymerization of thieno[3,4-b]thiophene (T34bT) and 3,4-ethylenedioxythiophene (EDOT). Langmuir 19:9479.
121. Kumar, A. and G.A. Sotzing. 2005. Poly(thieno[3,4-b]furan), a new low band gap conjugated polymer. Polym Prepr (Am Chem Soc Div Polym Chem) 46:969.
122. Kumar, A., Z. Buyukmumcu, and G.A. Sotzing. 2006. Poly(thieno[3,4-b]furan). A new low band gap conjugated polymer. Macromolecules 39:2723.
123. Kim, I.T., S.W. Lee, and J.Y. Lee. 2003. A new low bandgap conducting polymer. Polym Prepr (Am Chem Soc Div Polym Chem) 44:1163.
124. Gunatunga, S.R., et al. 1997. Synthesis and characterization of low band gap polymers. Synth Met 84:973.
125. Beyer, R., et al. 1998. Spectroelectrochemical and electrical characterization of low bandgap polymers. Synth Met 92:25.
126. Kalaji, M., P.J. Murphy, and G.O. Williams. 1999. Spectroelectrochemistry of bridged dithienyl derived polymers. Synth Met 101:123.
127. Mills, C.A., et al. 1999. Investigations into a low band gap, semiconducting polymer. Synth Met 102:1000.
128. Huang, H. and P.G. Pickup. 1997. In situ conductivity of a low band-gap conducting polymer: Measurement of intrinsic conductivity. Acta Polym 48:455.
129. Huang, H. and P.G. Pickup. 1999. Oxygen-modified poly(4-dicyanomethylene-4H-cyclopenta[2,1- b; 3,4- b 0] dithiophene): A tunable low band gap polymer. Chem Mater 11:1541.
130. Sannicolo, F., et al. 1998. Highly ordered poly(cyclopentabithiophenes) functionalized with crownether moieties for lithium- and sodium-sensing electrodes. Chem Mater 10:2167.
131. Loganathan, K., et al. 2003. D4,40 -dicyclopenta[2,1-b:3,4-b0]dithiophene. A conjugated bridging unit for low band gap conducting polymers. Chem Mater 15:1918.
132. Huang, H. and P.G. Pickup. 1998. A donor–acceptor conducting copolymer with a very low band gap and high intrinsic conductivity. Chem Mater 10:2212.
133. Karikomi, M., et al. 1995. New narrow-bandgap polymer composed of benzobis(1,2,5-thiadiazole) and thiophenes. J Am Chem Soc 117:6791.
134. Jayakannan, M., P.A. Van Hal, and R.A.J. Janssen. 2002. Synthesis, optical, and electrochemical properties of novel copolymers on the basis of benzothiadiazole and electron-rich arene units. J Polym Sci A Polym Chem 40:2360.
135. Anzenbacher, P., et al. 2004. Materials chemistry approach to anion-sensor design. Tetrahedron 60:11163.
136. Dmitry, A. and P. Anzenbacher. 2004. Sensing of aqueous phosphates by polymers with dual modes of signal transduction. J Am Chem Soc 126:4752.
137. Du Bois, C.J., et al. 2001. Multi-colored electrochromic polymers based on BEDOT-pyridines. Synth Met 119:321.
138. Chen, M., et al. 2004. 1 Micron wavelength photo- and electroluminescence from a conjugated polymer. Appl Phys Lett 84:3570.
139. Chen, M.X., et al. 2004. Low band gap donor–acceptor–donor polymers for infra-red electroluminescence and transistors. Synth Met 146:233.
140. Wang, X., et al. 2004. Infrared photocurrent spectral response from plastic solar cell with lowband- gap polyfluorene and fullerene derivative. Appl Phys Lett 85:5081.
141. Ajayaghosh, A. and J. Eldo. 2001. A novel approach towards low optical band gap polysquaraines. Org Lett 3:2595.
142. Eldo, J. and A. Ajayaghosh. 2002. New low band gap polymers: Control of optical and electronic properties in near infrared absorbing p-conjugated polysquaraines. Chem Mater 14:410.
143. Ajayaghosh, A. 2003. Intrinsically conducting low band gap polysquaraines via a–b type polycondensation. Int J Plast Technol 6:117.
144. Ajayaghosh, A. 2003. Donor–acceptor type low band gap polymers: Polysquaraines and related systems. Chem Soc Rev 32:181.
145. Ajayaghosh, A. 2005. Chemistry of squaraine-derived materials: Near-IR dyes, low band gap systems and cation sensors. Acc Chem Res 38:499.
146. Roncali, J., et al. 1994. Control of the bandgap of conducting polymers by rigidification of the p-conjugated system. J Chem Soc Chem Commun 2249.
147. Verlhac, P., et al. 1998. Polydithie´nyle´thyle`nes solubles de´rive´s de pre´curseurs a structure ponte´e. J Chim Phys 95:1274.
148. Blanchard, P., A. Riou, and J. Roncali. 1998. Electrosynthesis of a low band gap p-conjugated polymer from a multibridged dithienylethylene. J Org Chem 63:7107.
149. Ho, H.A., et al. 1995. Electrogenerated small bandgap p-conjugated polymers derived from substituted dithienylethylenes. J Chem Soc Chem Commun 2309.
150. Fusalba, F., et al. 2000. Poly(cyano-substituted diheteroareneethylene) as active electrode material for electrochemcial supercapacitors. Chem Mater 12:2581.
151. Sotzing, G.A. and J.R. Reynolds. 1995. Poly[trans-bis(3,4-ethlyenedioxythiophene)vinylene]: A low band-gap polymer with rapid redox switching capabilities between conducting transmissive and insulating absorptive states. J Chem Soc Chem Commun 703.
152. Sotzing, G.A., J.R. Reynolds, and P.J. Steel. 1996. Electrochromic conducting polymers via electrochemical polymerization of bis(2-(3,4-ethylendioxy)thienyl) monomers. Chem Mater 8:882.
153. Sotzing, G.A., J.L. Reddinger, and J.R. Reynolds. 1997. Redox active electochromic polymers from low oxidation monomers containing 3,4-ethylenedioxythiophene (EDOT). Synth Met 84:199.
154. Thomas, C.A. and J.R. Reynolds. 1999. Lowering the band gap of ethylenedioxythiophene polymers: Cyanovinylene-linked biheterocycles. Semiconducting polymers: Applications, properties, and Synthesis, eds. B.R. Hsieh and Y. Wei. Vol. Washington DC: American Chemical Society, p. 367
155. Sotzing, G.A., et al. 1998. Low band gap cyanovinylene polymers based on ethylenedioxythiophene. Macromolecules 31:3750.
156. Gallazzi, M.C., et al. 2002. A new low band gap dithienylene-fluorovinylene electrochromic polymer: An intriguing effect of silyl substitution on the polymerization reaction. J Mater Chem 12:2202.
157. Seshadri, V. and G.A. Sotzing. 2004. Polymerization of two unsymmetrical isomeric monomers based on thieno[3,4-b]thiophene containing cyanovinylene spacers. Chem Mater 16:5644.
158. Schlick, U., F. Teichert, and M. Hanack. 1998. Electrochemical and spectroelectrochemical investigations of small-bandgap p-conjugated polymers and their precursors. Synth Met 92:75.
159. Ho, H.A., et al. 1996. Thiophene-based conjugated oligomers and polymers with high electron affinity. Adv Mater 8:990.
160. Cheng, H. and R.L. Elsenbaumer. 1995. New precursors and polymerization route for the preparation of high molecular mass poly(3,4-dialkoxy-2,5-thienylenevinylene)s: Low band gap conductive polymers. J Chem Soc Chem Commun 1451.
161. Fu, Y., H. Cheng, and R.L. Elsenbaumer. 1997. Electron-rich thienylene-vinylene low bandgap polymers. Chem Mater 9:1720.
162. Bazzi, H.S. and H.F. Sleiman. 2002. Synthesis and self-assembly of conjugated polymer precursors containing dichlorocarbonate groups by living ring-opening metathesis polymerization. Macromolecules 35:624.
163. Chen, W.-C. and S.A. Jenekhe. 1995. Small-bandgap conducting polymers based on conjugated poly(heteroarylenemethines). Synthesis, structure, and properties. Macromolecules 28:465.
164. Zhang, Q., Y. Li, and M. Yang. 2004. A novel low band gap polymer PDTNTBQ. Synth Met 146:69.
165. Zhang, Q., Y. Li, and M. Yang. 2004. Novel soluble low band gap polymers. J Mater Sci 39:6089.
166. Benincori, T., et al. 2003. An electrochemically prepared small-bandgap poly(biheteroarylidenemethine): Poly{bi[(3,4-ethlyenedioxy)thienylene]methine}. Macromolecules 36:5114.
167. Chen, W.-C., et al. 2004. Theoretical and experimental characterization of small band gap poly(3,4- ethylenedioxythiophene methine)s. Macromolecules 37:5959.
168. Kiebooms, R. and F. Wudl. 1999. Synthesis and characterisation of poly(isothianaphthenemethine). Synth Met 101:40.
169. Neugebauer, H., et al. 1999. Infrared spectroelectrochemical investigations on the doping of soluble poly(isothianaphthtene methine) (PIM). J Chem Phys 110:12108.
170. Kiebooms, R.H.L., H. Goto, and K. Akagi. 2001. Synthesis of a new class of low-band-gap polymers with liquid crystalline substituents. Macromolecules 34:7989.
171. Aota, H., et al. 1997. Syntheses and properties of p-conjugated polymers containing chromophore. Water-soluble small-bandgap polymer backbone. Chem Lett 527.
172. Aota, H., et al. 1998. Syntheses and properties of p-conjugated polymers containing chromophore. Introduction of porphyrin units into main chain of water-soluble small band gap polymer. Chem Lett 335.
173. Goto, H., K. Akagi, and H. Shirakawa. 1997. Syntheses and properties of small-bandgap liquid crystalline conjugated polymers. Synth Met 84:385.
174. Akagi, K., et al. 1998. Small bandgap type liquid crystalline conjugated polymers. Mol Cryst Liq Cryst Sci Technol Sect A Mol Cryst Liq Cryst 316:201.
175. Yan, W., C.-S. Hsu, and Y. Wei. 2002. Synthesis and characterization of small band-gap conjugated polymers—poly(pyrrolyl methines). Chin Chem Lett 13:988.
176. Yan, W., et al. 2001. Synthesis and characterization of poly(pyrrolyl methine). Chin J Polym Sci 19:499.
177. Lee, Y., et al. 2001. A new narrow band gap electroactive polymer: Poly[2,5-bis{2-(3,4-ethylenedioxy) thienyl}silole]. Chem Mater 13:2234.
178. Lee, Y., et al. 2001. A new silole containing low band gap electroactive polymer. Synth Met 119:77.
179. Takimiya, K., et al. 2002. Synthesis, structures, and properties of two isomeric naphthodithiophenes and their methyl, methylthio, and 2-thienyl derivatives; application to conductive chargetransfer complexes and low-bandgap polymers. Bull Chem Soc Jpn 75:1795.
180. Casado, J., et al. 2004. A Raman and computational study of two dithienyl naphthodithiophenes: Synthesis and characterization of new polymers showing low band gap optical and electroactive features. J Phys Chem B 108:7611.
181. D’ilario, L., et al. 1995. Bis(ethynyl)-polymers. J Mater Sci 30:4273.
182. Kean, C.L. and P.G. Pickup. 2001. A low band gap conjugated metallopolymer with nickel bis(dithiolene) crosslinks. Chem Commun 815.
183. Tsuda, A. and A. Osuka. 2002. Discrete conjugated porphyrin tapes with an exceptionally small bandgap. Adv Mater 14:75.