Synthesis and light-emitting behavior of silicon-bridged fluorene copolymers bearing oligoarylenevinylene chromophore

Synthesis and light-emitting behavior of silicon-bridged fluorene copolymers bearing oligoarylenevinylene chromophore

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ABSTRACT Silicon-bridged fluorene copolymers bearing oligoarylenevinylene chromophore with longer effective conjugation length than terfluorene were prepared by the Suzuki coupling copolymerization, where the polymer structure was designed so that the absorption spectrum of energy-accepting oligoarylenevinylene chromophore can overlap with the emission spectrum of energy-donating terfluorene chromophore. The content of oligoarylenevinylene segment in 2A5, 2A10, 2A20, 2A48, and 2A100 could be well controlled by the monomer feed ratio as evidenced by the UV spectra of copolymers in solution. Since the fluorescence from oligoarylenevinylene segment was observed in copolymers and the polymer blend system did not afford longer wavelength emission in dilute solution, the importance of intra-polymer chain energy transfer between chromophores was demonstrated. The fluorescence peaks of 2B13, 2C11, and 2D3 ascribed to the emission from oligoarylenevinylene segment were observed in thin film through the intra- and inter-polymer chain energy transfer. SIMILAR CONTENT BEING VIEWED BY OTHERS ENABLING NONCONJUGATED POLYESTERS EMIT FULL-SPECTRUM FLUORESCENCE FROM BLUE TO NEAR-INFRARED Article Open access 08 January 2024 ALL-ORGANIC POLYMERIC MATERIALS WITH HIGH REFRACTIVE INDEX AND EXCELLENT TRANSPARENCY Article Open access 14 June 2023 LONG-WAVE INFRARED TRANSPARENT SULFUR POLYMERS ENABLED BY SYMMETRIC THIOL CROSS-LINKER Article Open access 19 May 2023 ARTICLE PDF REFERENCES * A. Yokoyama, R. Miyakoshi, and T. Yokozawa, _Macromolecules_, 37, 1169 (2004). * R. Miyakoshi, A. Yokoyama, and T. Yokozawa, _Macromol. Rapid Commun._, 25, 1663 (2004). * R. Miyakoshi, A. Yokoyama, and T. Yokozawa, _J. Am. Chem. Soc._, 127, 17542 (2005). * E. E. Sheina, J. Liu, M. C. Iovu, D. W. Laird, and R. D. McCullough, _Macromolecules_, 37, 3526 (2004). * M. C. Iovu, E. E. Sheina, R. R. Gil, and R. D. McCullough, _Macromolecules_, 38, 8649 (2005). * M. Jeffries-El, G. Sauvé, and R. D. McCullough, _Macromolecules_, 38, 10346 (2005). * R.-M. Chen, K.-M. Chien, K.-T. Wong, B.-Y. Jin, and T.-Y. Luh, _J. Am. Chem. Soc._, 119, 11321 (1997). * Y.-J. Miao and G. C. Bazan, _Macromolecules_, 30, 7414 (1997). * H. Li and R. West, _Macromolecules_, 31, 2866 (1998). * D. S. Kim and S. C. Shim, _J. Polym. Sci., Part A: Polym. Chem._, 37, 2263 (1999). * S. H. Jung, H. K. Kim, S. H. Kim, Y. H. Kim, S. C. Jeoung, and D. Kim, _Macromolecules_, 33, 9277 (2000). * A. Mori, E. Takehisa, H. Kajiro, Y. Nishihara, and T. Hiyama, _Macromolecules_, 33, 1115 (2000). * J. Ohshita, A. Takata, H. Kai, A. Kunai, K. Komaguchi, M. Shiotani, A. Adachi, K. Sakamaki, K. Okita, Y. Harima, Y. Kunugi, K. Yamashita, and M. Ishikawa, _Organometallics_, 19, 4492 (2000). * X. Jiang, Y. Harima, K. Yamashita, A. Naka, K. K. Lee, and M. Ishikawa, _J. Mater. Chem._, 13, 785 (2003). * K. Takagi, H. Kakiuchi, and M. Suzuki, _Kobunshi Ronbunshu_, 63, 663 (2006). * K. Takagi, H. Kakiuchi, Y. Yuki, and M. Suzuki, _J. Polym. Sci., Part A: Polym. Chem._, 45, 4786 (2007). * X.-H. Zhou, Y.-H. Niu, F. Huang, M. S. Liu, and A. K.-Y. Jen, _Macromolecules_, 40, 3015 (2007). * For a polymer containing silole segment, see: K. L. Chan, M. J. McKiernan, C. R. Towns, and A. B. Holmes, _J. Am. Chem. Soc._, 127, 7662 (2005). * S. Kyushin, M. Ikarugi, M. Goto, H. Hiratsuka, and H. Matsumoto, _Organometallics_, 15, 1067 (1996). * H. Maeda, Y. Inoue, H. Ishida, and K. Mizuno, _Chem. Lett._, 30, 1224 (2001). * S. Yamaguchi and K. Tamao, _J. Chem. Soc., Dalton Trans._ 3693, 1998. * S. Yamaguchi and K. Tamao, _J. Organomet. Chem._, 653, 223 (2002). * S. E. Webber, _Chem. Rev._, 90, 1469 (1990). * A. Adronov, S. L. Gilat, J. M. J. Fréchet, K. Ohta, F. V. R. Neuwahl, and G. R. Fleming, _J. Am. Chem. Soc._, 122, 1175 (2000). * M. A. Fox, _Acc. Chem. Res._, 32, 201 (1999). * C. Devadoss, P. Bharathi, and J. S. Moore, _J. Am. Chem. Soc._, 118, 9635 (1996). * J. M. Serin, D. W. Brousmiche, and J. M. J. Fréchet, _Chem. Commun._, 2002, 2605. * C. Hippius, F. Schlosser, M. O. Vysotsky, V. Böhmer, and F. Würthner, _J. Am. Chem. Soc._, 128, 3870 (2006). * C. A. van Walree, M. R. P. Roest, W. Schuddeboom, L. W. Jenneskens, J. W. Verhoeven, J. M. Warman, H. Kooijman, and A. L. Spek, _J. Am. Chem. Soc._, 118, 8395 (1996). * A. Zehnacker, F. Lahmani, C. A. Van Walree, and L. W. Jenneskens, _J. Phys. Chem. A_, 104, 1377 (2000). * T. Förster, _Ann. Phys._, 437, 55 (1948). * Y.-J. Cheng, T.-Y. Hwu, J.-H. Hsu, and T.-Y. Luh, _Chem. Commun._ 1978, (2002). * Y.-J. Cheng and T.-Y. Luh, _Chem.-Eur. J._, 10, 5361 (2004). * Y.-J. Cheng, S. Basu, S.-J. Luo, and T.-Y. Luh, _Macromolecules_, 38, 1442 (2005). * W. You, S. Cao, Z. Hou, and L. Yu, _Macromolecules_, 36, 7014 (2003). * T. Ahn, S.-Y. Song, and H.-K. Shim, _Macromolecules_, 33, 6764 (2000). Download references AUTHOR INFORMATION AUTHORS AND AFFILIATIONS * Department of Materials Science and Engineering, Nagoya Institute of Technology, Gokiso, Showa, 466-8555, Nagoya, Japan Koji Takagi, Ai Tahara & Hiroki Kakiuchi Authors * Koji Takagi View author publications You can also search for this author inPubMed Google Scholar * Ai Tahara View author publications You can also search for this author inPubMed Google Scholar * Hiroki Kakiuchi View author publications You can also search for this author inPubMed Google Scholar CORRESPONDING AUTHOR Correspondence to Koji Takagi. RIGHTS AND PERMISSIONS Reprints and permissions ABOUT THIS ARTICLE CITE THIS ARTICLE Takagi, K., Tahara, A. & Kakiuchi, H. Synthesis and Light-Emitting Behavior of Silicon-Bridged Fluorene Copolymers Bearing Oligoarylenevinylene Chromophore. _Polym J_ 41, 733–738 (2009). https://doi.org/10.1295/polymj.PJ2009088 Download citation * Received: 15 April 2009 * Accepted: 26 May 2009 * Published: 09 July 2009 * Issue Date: 01 September 2009 * DOI: https://doi.org/10.1295/polymj.PJ2009088 SHARE THIS ARTICLE Anyone you share the following link with will be able to read this content: Get shareable link Sorry, a shareable link is not currently available for this article. Copy to clipboard Provided by the Springer Nature SharedIt content-sharing initiative KEYWORDS * Silicon * Fluorene * Copolymer * Energy Transfer * Light-Emission

ABSTRACT Silicon-bridged fluorene copolymers bearing oligoarylenevinylene chromophore with longer effective conjugation length than terfluorene were prepared by the Suzuki coupling


copolymerization, where the polymer structure was designed so that the absorption spectrum of energy-accepting oligoarylenevinylene chromophore can overlap with the emission spectrum of


energy-donating terfluorene chromophore. The content of oligoarylenevinylene segment in 2A5, 2A10, 2A20, 2A48, and 2A100 could be well controlled by the monomer feed ratio as evidenced by


the UV spectra of copolymers in solution. Since the fluorescence from oligoarylenevinylene segment was observed in copolymers and the polymer blend system did not afford longer wavelength


emission in dilute solution, the importance of intra-polymer chain energy transfer between chromophores was demonstrated. The fluorescence peaks of 2B13, 2C11, and 2D3 ascribed to the


emission from oligoarylenevinylene segment were observed in thin film through the intra- and inter-polymer chain energy transfer. SIMILAR CONTENT BEING VIEWED BY OTHERS ENABLING


NONCONJUGATED POLYESTERS EMIT FULL-SPECTRUM FLUORESCENCE FROM BLUE TO NEAR-INFRARED Article Open access 08 January 2024 ALL-ORGANIC POLYMERIC MATERIALS WITH HIGH REFRACTIVE INDEX AND


EXCELLENT TRANSPARENCY Article Open access 14 June 2023 LONG-WAVE INFRARED TRANSPARENT SULFUR POLYMERS ENABLED BY SYMMETRIC THIOL CROSS-LINKER Article Open access 19 May 2023 ARTICLE PDF


REFERENCES * A. Yokoyama, R. Miyakoshi, and T. Yokozawa, _Macromolecules_, 37, 1169 (2004). * R. Miyakoshi, A. Yokoyama, and T. Yokozawa, _Macromol. Rapid Commun._, 25, 1663 (2004). * R.


Miyakoshi, A. Yokoyama, and T. Yokozawa, _J. Am. Chem. Soc._, 127, 17542 (2005). * E. E. Sheina, J. Liu, M. C. Iovu, D. W. Laird, and R. D. McCullough, _Macromolecules_, 37, 3526 (2004). *


M. C. Iovu, E. E. Sheina, R. R. Gil, and R. D. McCullough, _Macromolecules_, 38, 8649 (2005). * M. Jeffries-El, G. Sauvé, and R. D. McCullough, _Macromolecules_, 38, 10346 (2005). * R.-M.


Chen, K.-M. Chien, K.-T. Wong, B.-Y. Jin, and T.-Y. Luh, _J. Am. Chem. Soc._, 119, 11321 (1997). * Y.-J. Miao and G. C. Bazan, _Macromolecules_, 30, 7414 (1997). * H. Li and R. West,


_Macromolecules_, 31, 2866 (1998). * D. S. Kim and S. C. Shim, _J. Polym. Sci., Part A: Polym. Chem._, 37, 2263 (1999). * S. H. Jung, H. K. Kim, S. H. Kim, Y. H. Kim, S. C. Jeoung, and D.


Kim, _Macromolecules_, 33, 9277 (2000). * A. Mori, E. Takehisa, H. Kajiro, Y. Nishihara, and T. Hiyama, _Macromolecules_, 33, 1115 (2000). * J. Ohshita, A. Takata, H. Kai, A. Kunai, K.


Komaguchi, M. Shiotani, A. Adachi, K. Sakamaki, K. Okita, Y. Harima, Y. Kunugi, K. Yamashita, and M. Ishikawa, _Organometallics_, 19, 4492 (2000). * X. Jiang, Y. Harima, K. Yamashita, A.


Naka, K. K. Lee, and M. Ishikawa, _J. Mater. Chem._, 13, 785 (2003). * K. Takagi, H. Kakiuchi, and M. Suzuki, _Kobunshi Ronbunshu_, 63, 663 (2006). * K. Takagi, H. Kakiuchi, Y. Yuki, and M.


Suzuki, _J. Polym. Sci., Part A: Polym. Chem._, 45, 4786 (2007). * X.-H. Zhou, Y.-H. Niu, F. Huang, M. S. Liu, and A. K.-Y. Jen, _Macromolecules_, 40, 3015 (2007). * For a polymer containing


silole segment, see: K. L. Chan, M. J. McKiernan, C. R. Towns, and A. B. Holmes, _J. Am. Chem. Soc._, 127, 7662 (2005). * S. Kyushin, M. Ikarugi, M. Goto, H. Hiratsuka, and H. Matsumoto,


_Organometallics_, 15, 1067 (1996). * H. Maeda, Y. Inoue, H. Ishida, and K. Mizuno, _Chem. Lett._, 30, 1224 (2001). * S. Yamaguchi and K. Tamao, _J. Chem. Soc., Dalton Trans._ 3693, 1998. *


S. Yamaguchi and K. Tamao, _J. Organomet. Chem._, 653, 223 (2002). * S. E. Webber, _Chem. Rev._, 90, 1469 (1990). * A. Adronov, S. L. Gilat, J. M. J. Fréchet, K. Ohta, F. V. R. Neuwahl, and


G. R. Fleming, _J. Am. Chem. Soc._, 122, 1175 (2000). * M. A. Fox, _Acc. Chem. Res._, 32, 201 (1999). * C. Devadoss, P. Bharathi, and J. S. Moore, _J. Am. Chem. Soc._, 118, 9635 (1996). * J.


M. Serin, D. W. Brousmiche, and J. M. J. Fréchet, _Chem. Commun._, 2002, 2605. * C. Hippius, F. Schlosser, M. O. Vysotsky, V. Böhmer, and F. Würthner, _J. Am. Chem. Soc._, 128, 3870 (2006).


* C. A. van Walree, M. R. P. Roest, W. Schuddeboom, L. W. Jenneskens, J. W. Verhoeven, J. M. Warman, H. Kooijman, and A. L. Spek, _J. Am. Chem. Soc._, 118, 8395 (1996). * A. Zehnacker, F.


Lahmani, C. A. Van Walree, and L. W. Jenneskens, _J. Phys. Chem. A_, 104, 1377 (2000). * T. Förster, _Ann. Phys._, 437, 55 (1948). * Y.-J. Cheng, T.-Y. Hwu, J.-H. Hsu, and T.-Y. Luh, _Chem.


Commun._ 1978, (2002). * Y.-J. Cheng and T.-Y. Luh, _Chem.-Eur. J._, 10, 5361 (2004). * Y.-J. Cheng, S. Basu, S.-J. Luo, and T.-Y. Luh, _Macromolecules_, 38, 1442 (2005). * W. You, S. Cao,


Z. Hou, and L. Yu, _Macromolecules_, 36, 7014 (2003). * T. Ahn, S.-Y. Song, and H.-K. Shim, _Macromolecules_, 33, 6764 (2000). Download references AUTHOR INFORMATION AUTHORS AND AFFILIATIONS


* Department of Materials Science and Engineering, Nagoya Institute of Technology, Gokiso, Showa, 466-8555, Nagoya, Japan Koji Takagi, Ai Tahara & Hiroki Kakiuchi Authors * Koji Takagi


View author publications You can also search for this author inPubMed Google Scholar * Ai Tahara View author publications You can also search for this author inPubMed Google Scholar * Hiroki


Kakiuchi View author publications You can also search for this author inPubMed Google Scholar CORRESPONDING AUTHOR Correspondence to Koji Takagi. RIGHTS AND PERMISSIONS Reprints and


permissions ABOUT THIS ARTICLE CITE THIS ARTICLE Takagi, K., Tahara, A. & Kakiuchi, H. Synthesis and Light-Emitting Behavior of Silicon-Bridged Fluorene Copolymers Bearing


Oligoarylenevinylene Chromophore. _Polym J_ 41, 733–738 (2009). https://doi.org/10.1295/polymj.PJ2009088 Download citation * Received: 15 April 2009 * Accepted: 26 May 2009 * Published: 09


July 2009 * Issue Date: 01 September 2009 * DOI: https://doi.org/10.1295/polymj.PJ2009088 SHARE THIS ARTICLE Anyone you share the following link with will be able to read this content: Get


shareable link Sorry, a shareable link is not currently available for this article. Copy to clipboard Provided by the Springer Nature SharedIt content-sharing initiative KEYWORDS * Silicon *


Fluorene * Copolymer * Energy Transfer * Light-Emission