Abstract
Two novel π-conjugated polymers composed of alkyl carbazole/dialkoxyphenylene and squaraine units were synthesized by Sonogashira cross-coupling reactions. The structures and properties of these copolymers were characterized using FT-IR, NMR, UV–Vis, gel permeation chromatography and cyclic voltammetry (CV). Both polymers possess adequate thermal stability and exhibit good solubility in common organic solvents such as chloroform, THF, and toluene. The polymer films show intense and broad visible and near IR absorption with the long wavelength absorption maximum peaks of 796 and 851 nm for P1 and P2, respectively, which are apparently red-shifted compared with poly(phenyleneethynylene). CV studies reveal that the band gaps of these copolymers are about 1.45 eV, implying that the resulted polymers may be promising candidates for solar cells.
Similar content being viewed by others
References
Schmidt-Mende L, Fechtenkotter A, Mullen K (2001) Science 293:1119
Goris L, Haenen K, Nesladek M (2005) J Mater Sci 40:1413. doi:https://doi.org/10.1007/s10853-005-0576-0
Chen JW, Cao Y (2009) Acc Chem Res 42:1709
Qiao F, Liu A, Zhou Y (2009) J Mater Sci 44:1283. doi:https://doi.org/10.1007/s10853-009-3280-7
Thompson BC, Frechet JMJ (2008) Angew Chem Int Ed 47:58
Dennler G, Scharber MC, Brabec CJ (2009) Adv Mater 21:1323
Kim JY, Lee K, Coates NE, Moses D, Nguyen TQ, Dante M, Heeger AJ (2007) Science 317:222
Liang YY, Xu Z, Xia JB, Tsai ST, Wu Y, Li G, Ray C, Yu LP (2010) Adv Mater 22:1
Bunz UHF (2009) Macromol Rapid Commun 30:772
Ashraf RS, Shahid M, Klemm E, Al-Ibrahim M, Sensfuss S (2006) Macromol Rapid Commun 27:1454
Ashraf RS, Klemm E (2005) J Polym Sci Part A Polym Chem 43:6445
Bagnis D, Beverina L, Huang H, Silvestri F, Yao Y, Yan H, Pagani GA, Marks TJ, Facchetti A (2010) J Am Chem Soc 132:4074
Geiger T, Kuster S, Yum J, Moon S, Nazeeruddin M, Grätzel M, Nüesch F (2009) Adv Funct Mater 19:2720
Eldo J, Ajayaghosh A (2002) Chem Mater 14:410
Ajayaghosh A (2003) Chem Soc Rev 32:181
Roncali J (1997) Chem Rev 97:173
Brédas JL (1985) J Chem Phys 82:3808
Hunt JT, Mitt T, Borzilleri R, Gullo-Brown J, Fargnoli J, Fink B, Han WC, Mortillo S, Vite G, Wautlet B, Wong T, Yu C, Zheng XP, Bhide R (2004) J Med Chem 47:4054
Aldabbagh F, Bowman WR, Mann E (1997) Tetrahedron Lett 38:7937
Egbe DAM, Bader C, Klemm E, Ding LM, Karasz FE, Grummt UW, Birckner E (2003) Macromolecules 36:9303
Tsai HC, Yu IC, Chang PH, Yu DC, Hsiue GH (2007) Macromol Rapid Commun 28:334
Chi JH, Park SH, Lee CL, Kim JJ, Jung JC (2007) Macromol Mater Eng 292:844
Dieck HA, Heck RF (1975) J Organomet Chem 93:259
Sonogashira K, Tohda Y, Hagihara N (1975) Tetrahedron Lett 16:4467
Wu PT, Kim FS, Champion RD, Jenekhe SA (2008) Macromolecules 41:7021
Zou YP, Tan ZA, Huo LJ, Li YF (2008) Polym Adv Technol 19:865
Kijima M, Koguchi R, Abe S (2005) Chem Lett 34:900
Chen H, Cai XR, Xu ZG, Zhang T, Song BF, Li Y, Jiang Q, Xie MG (2008) Polym Bull 60:581
Bredas JL, Silbey R, Boudreaux DS (1983) J Am Chem Soc 105:6555
Tsai JH, Chueh CC, Lai MH (2009) Macromolecules 42:1897
Acknowledgements
This study was supported by the key foundation of education ministry of China (20070610053) and Sichuan Province Foundation for Youths (2008JY0050). The authors also acknowledge the Analytical & Testing Center of Sichuan University for the NMR measurements.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Zhang, W., Tao, F., Meng, Kg. et al. Synthesis and characterization of novel poly(aryleneethynylene)s derived from squaraines for photovoltaic applications. J Mater Sci 46, 5363–5370 (2011). https://doi.org/10.1007/s10853-011-5474-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10853-011-5474-z