Department of Polymer Science and Engineering, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China
ljfan@suda.edu.cn
收稿:2019-02-15,
修回:2019-2-28,
录用:2019-3-1,
网络首发:2019-04-01,
纸质出版:2019-11
Scan QR Code
Wu, Y. Z.; Zhang, Y. C.; Chen, J. J.; Fan, L. J. Synthesis of conjugated polymers containing diketopyrrolopyrrole (DPP) building block and the photophysical study. Chinese J. Polym. Sci. 2019, 37, 1092–1098.
Ying-Zhong Wu, Yi-Chen Zhang, Jia-Jun Chen, et al. Synthesis of Conjugated Polymers Containing Diketopyrrolopyrrole (DPP) Building Block and the Photophysical Study[J]. Chinese Journal of Polymer Science, 2019, 37(11): 1092-1098.
Wu, Y. Z.; Zhang, Y. C.; Chen, J. J.; Fan, L. J. Synthesis of conjugated polymers containing diketopyrrolopyrrole (DPP) building block and the photophysical study. Chinese J. Polym. Sci. 2019, 37, 1092–1098. DOI: 10.1007/s10118-019-2248-6.
Ying-Zhong Wu, Yi-Chen Zhang, Jia-Jun Chen, et al. Synthesis of Conjugated Polymers Containing Diketopyrrolopyrrole (DPP) Building Block and the Photophysical Study[J]. Chinese Journal of Polymer Science, 2019, 37(11): 1092-1098. DOI: 10.1007/s10118-019-2248-6.
Sonogashira coupling of two different diketopyrrolopyrrole (DPP)-containing dihaloarenes with the same aromatic bisalkyne resulted in two new conjugated polymers with the same backbone but different pendant groups on the DPP moiety. The polymers were found to have designed chemical structures
via
structural characterizations in comparison with three monomers. The molecular weight measurement further demonstrated the formation of polymers with polydispersity index around 2
consistent with the polycondensation nature of the polymerization based on Sonogashira coupling. Both polymers could dissolve in many organic solvents
and the one with long alkyl side group on DPP moiety had better solubility. Photophysical investigation showed that both polymers had typical absorption/emission of conjugated polymers
and varying the solvent did not have large influence. Compared with other polar solvents
toluene reduced the quantum yield of fluorescence of the polymers
especially for the one with long alkyl pedant group
accompanying with slight red-shift in absorption/emission. The difference in the absorption/emission wavelengths between the polymers was similar to that between the corresponding monomers. Adding water into the THF solution of polymers reduced the emission intensity but no red-shift was observed. Discussion about the structure-property relationships was carried out in detail.
Grimsdale, A. C.; Chan, K. L.; Martin, R. E.; Jokisz, P. G.; Holmes, A. B . Synthesis of light-emitting conjugated polymers for applications in electroluminescent devices . Chem. Rev. , 2009 . 109 897 - 1091 . DOI: 10.1021/cr000013v http://doi.org/10.1021/cr000013v .
Günes, S.; Neugebauer, H.; Sariciftci, N. S . Conjugated polymer-based organic solar cells . Chem. Rev. , 2007 . 107 1324 - 1338 . DOI: 10.1021/cr050149z http://doi.org/10.1021/cr050149z .
Bin, H.; Li, Y . Recent research progress of photovoltaic materials for nonfullerene polymer solar cells . Acta Polymerica Sinica (in Chinese) , 2017 . 1444 - 1461 . DOI: 10.11777/j.issn1000-3304.2017.17119 http://doi.org/10.11777/j.issn1000-3304.2017.17119 .
Zhao, L.; Lin, Z . Crafting semiconductor organic-inorganic nanocomposites via placing conjugated polymers in intimate contact with nanocrystals for hybrid solar cells . Adv. Mater. , 2012 . 24 4353 - 4368 . DOI: 10.1002/adma.201201196 http://doi.org/10.1002/adma.201201196 .
Lyu, Y.; Pu, K . Recent advances of activatable molecular probes based on semiconducting polymer nanoparticles in sensing and imaging . Adv. Sci. , 2017 . 4 1600481 DOI: 10.1002/advs.201600481 http://doi.org/10.1002/advs.201600481 .
Fan, L. J.; Zhang, Y.; Murphy, C. B.; Angell, S. E.; Parker, M. F. L.; Flynn, B. R.; Jones, W. E . Fluorescent conjugated polymer molecular wire chemosensors for transition metal ion recognition and signaling . Coord. Chem. Rev. , 2009 . 253 410 - 422 . DOI: 10.1016/j.ccr.2008.03.008 http://doi.org/10.1016/j.ccr.2008.03.008 .
Zhang, E.; Liu, L.; Lv, F.; Wang, S . Water-soluble conjugated polymers for biosensor applications . Acta Polymerica Sinica (in Chinese) , 2018 . 186 - 197 . DOI: 10.11777/j.issn1000-3304.2018.17269 http://doi.org/10.11777/j.issn1000-3304.2018.17269 .
McQuade, D. T.; Pullen, A. E.; Swager, T. M . Conjugated polymer-based chemical sensors . Chem. Rev. , 2000 . 100 2537 - 2574 . DOI: 10.1021/cr9801014 http://doi.org/10.1021/cr9801014 .
McAfee, S. M.; Dayneko, S. V.; Hendsbee, A. D.; Josse, P.; Blanchard, P.; Cabanetos, C.; Welch, G. C . Applying direct heteroarylation synthesis to evaluate organic dyes as the core component in PDI-based molecular materials for fullerene-free organic solar cells . J. Mater. Chem. A , 2017 . 5 11623 - 11633 . DOI: 10.1039/C7TA00318H http://doi.org/10.1039/C7TA00318H .
Kaur, M.; Choi, D. H . Diketopyrrolopyrrole: Brilliant red pigment dye-based fluorescent probes and their applications . Chem. Soc. Rev. , 2015 . 44 58 - 77 . DOI: 10.1039/C4CS00248B http://doi.org/10.1039/C4CS00248B .
Shen, X. Y.; Wang, Y. J.; Zhang, H.; Qin, A.; Sun, J. Z.; Tang, B. Z . Conjugates of tetraphenylethene and diketopyrrolopyrrole: Tuning the emission properties with phenyl bridges . Chem. Commun. , 2014 . 50 8747 - 8750 . DOI: 10.1039/C4CC03024A http://doi.org/10.1039/C4CC03024A .
Tang, S.; Zadeh, E. H. G.; Kim, B.; Toomey, N. T.; Bondarc, M. V.; Belfield, K. D . Protein-induced fluorescence enhancement of two-photon excitable water-soluble diketopyrrolopyrroles . Org. Biomol. Chem. , 2017 . 15 6511 - 6519 . DOI: 10.1039/C7OB01397C http://doi.org/10.1039/C7OB01397C .
Zong, S.; Wang, X.; Lin, W.; Liu, S.; Zhang, W . Simple D-A-D structural bisbithiophenyl diketopyrrolopyrrole as efficient bioimaging and photothermal agents . Bioconjugate Chem. , 2018 . 29 2619 - 2627 . DOI: 10.1021/acs.bioconjchem.8b00333 http://doi.org/10.1021/acs.bioconjchem.8b00333 .
Zeng, W.; Zhou, Q.; Zhang, H.; Qi, X . One-coat epoxy coating development for the improvement of UV stability by DPP pigments . Dyes Pigments , 2018 . 151 157 - 164 . DOI: 10.1016/j.dyepig.2017.12.058 http://doi.org/10.1016/j.dyepig.2017.12.058 .
Qu, S.; Tian, H . Diketopyrrolopyrrole (DPP)-based materials for organic photovoltaics . Chem. Commun. , 2012 . 48 3039 - 3051 . DOI: 10.1039/c2cc17886a http://doi.org/10.1039/c2cc17886a .
Yang, J.; Chen, J.; Sun, Y.; Shi, L.; Guo, Y.; Wang, S.; Liu, Y . Design and synthesis of novel conjugated polymers for applications in organic field-effect transistors . Acta Polymerica Sinica (in Chinese) , 2017 . 1082 - 1096 . DOI: 10.11777/j.issn1000-3304.2017.17020 http://doi.org/10.11777/j.issn1000-3304.2017.17020 .
Li, W.; Hendriks, K. H.; Wienk, M. M.; Janssen, R. A. J . Diketopyrrolopyrrole polymers for organic solar cells . Acc. Chem. Res. , 2016 . 49 78 - 85 . DOI: 10.1021/acs.accounts.5b00334 http://doi.org/10.1021/acs.accounts.5b00334 .
Zhang, Z.; Liu, Z.; Yan, K.; Li, H.; Liu, W.; Lu, X.; Li, H.; Chen, H.; Li, C . Photovoltaic properties of DPP-based two- and three-component polymers . Acta Polymerica Sinica (in Chinese) , 2018 . 295 - 303 . DOI: 10.11777/j.issn1000-3304.2018.17253 http://doi.org/10.11777/j.issn1000-3304.2018.17253 .
Deng, Y.; Xiao, H.; Qiao, H.; Tan, S . Synthesis and photoelectric performance of conjugated polymers with ullazine unit . Acta Polymerica Sinica (in Chinese) , 2017 . 922 - 929 . DOI: 10.11777/j.issn1000-3304.2017.16314 http://doi.org/10.11777/j.issn1000-3304.2017.16314 .
Qu, Y.; Wu, Y.; Gao, Y.; Qu, S.; Yang, L.; Hua, J . Diketopyrrolopyrrole-based fluorescent conjugated polymer for application of sensing fluoride ion and bioimaging . Sens. Actuators B , 2014 . 197 13 - 19 . DOI: 10.1016/j.snb.2014.02.065 http://doi.org/10.1016/j.snb.2014.02.065 .
Lin, S.; Liu, S.; Zou, H.; Zeng, W.; Wang, L.; Beuerman, R.; Cao, D . Synthesis of diketopyrrolopyrrole-containing conjugated polyelectrolytes for naked-eye detection of DNA . J. Polym. Sci., Part A: Polym. Chem. , 2011 . 49 3882 - 3889 . DOI: 10.1002/pola.24829 http://doi.org/10.1002/pola.24829 .
He, F.; Liu, L.; Li, L . Water-soluble conjugated polymers for amplified fluorescence detection of template-independent DNA elongation catalyzed by polymerase . Adv. Funct. Mater. , 2011 . 21 3143 - 3149 . DOI: 10.1002/adfm.201100216 http://doi.org/10.1002/adfm.201100216 .
Yang, J.; Wang, H.; Chen, J.; Huang, J.; Jiang, Y.; Zhang, J.; Shi, L.; Sun, Y.; Wei, Z.; Yu, G.; Guo, Y.; Wang, S.; Liu, Y . Bis-diketopyrrolopyrrole moiety as a promising building block to enable balanced ambipolar polymers for flexible transistors . Adv. Mater. , 2017 . 29 1606162 DOI: 10.1002/adma.v29.22 http://doi.org/10.1002/adma.v29.22 .
Wang, B.; Sonar, P.; Manzhos, S.; Haick, H . Diketopyrrolopyrrole copolymers based chemical sensors for the detection and discrimination of volatile organic compounds . Sens. Actuators B , 2017 . 251 49 - 56 . DOI: 10.1016/j.snb.2017.04.167 http://doi.org/10.1016/j.snb.2017.04.167 .
Gao, Y.; Bai, J.; Sui, Y.; Han, Y.; Deng, Y.; Tian, H.; Geng, Y.; Wang, F . High mobility ambipolar diketopyrrolopyrrole-based conjugated polymers synthesized via direct arylation polycondensation: Influence of thiophene moieties and side chains . Macromolecules , 2018 . 51 8752 - 8760 . DOI: 10.1021/acs.macromol.8b01112 http://doi.org/10.1021/acs.macromol.8b01112 .
Shen, H.; Kou, C.; He, M.; Yang, H.; Liu, K . Synthesis and surfactochromicity of 1,4-diketopyrrolo[3,4-c] pyrrole (DPP)-based anionic conjugated polyelectrolytes . J. Polym. Sci., Part A: Polym. Chem. , 2014 . 52 739 - 751 . DOI: 10.1002/pola.v52.6 http://doi.org/10.1002/pola.v52.6 .
Lee, J. B.; Kim, K. H.; Hong, C. S.; Choi, D. H . High-performance amorphous donor-acceptor conjugated polymers containing X-shaped anthracene-based monomer and 2,5-bis(2-octyldodecyl)pyrrolo[3,4- c ] pyrrole-1,4(2 H ,5 H )-dione for organic thin-film transistors . J. Polym. Sci., Part A: Polym. Chem. , 2012 . 50 2809 - 2818 . DOI: 10.1002/pola.26078 http://doi.org/10.1002/pola.26078 .
Sen, C. P.; Shrestha, R. G.; Shrestha, L. K.; Ariga, K.; Valiyaveettil, S . Low-band-gap BODIPY conjugated copolymers for sensing volatile organic compounds . Chem. Eur. J. , 2015 . 21 17344 - 17354 . DOI: 10.1002/chem.201502939 http://doi.org/10.1002/chem.201502939 .
Zhang, G.; Liu, K.; Lia, Y.; Yang, M . Novel poly(phenylene ethynylene)-type conjugated polymers containing diketopyrrolopyrrole or triphenylpyrazoline units in the main chain: Synthesis, characterization and photophysical properties . Polym. Int. , 2009 . 58 665 - 673 . DOI: 10.1002/pi.2576 http://doi.org/10.1002/pi.2576 .
Palai, A. K.; Mishra, S. P.; Kumar, A.; Srivastava, R.; Kamalasanan, M. N.; Patri, M . Synthesis and characterization of alternative donor-acceptor arranged poly(arylene ethynylene)s derived from 1,4-diketo-3,6-diphenylpyrrolo-[3,4-c] pyrrole (DPP) . Eur. Polym. J. , 2010 . 46 1940 - 1951 . DOI: 10.1016/j.eurpolymj.2010.07.004 http://doi.org/10.1016/j.eurpolymj.2010.07.004 .
Zhao, Y. J.; Miao, K.; Zhu, Z.; Fan, L. J . Fluorescence quenching of a conjugated polymer by synergistic amine-carboxylic acid and π - π interactions for selective detection of aromatic amines in aqueous solution . ACS Sens. , 2017 . 2 842 - 847 . DOI: 10.1021/acssensors.7b00245 http://doi.org/10.1021/acssensors.7b00245 .
Wu, W.; Xu, H.; Shen, D.; Qiu, T.; Fan, L. J . One-step synthesis of a thienylenepyridazinylenethienylene-based coil-rod-coil copolymer with enhanced emission and improved fluorescence stability . J. Polym. Sci., Part A: Polym. Chem. , 2013 . 51 1636 - 1644 . DOI: 10.1002/pola.26535 http://doi.org/10.1002/pola.26535 .
Zhang, H.; Shao, Y.; Chen, H.; Miao, K.; Fan, L. J . Poly(perylene- alt -phenyleneethynylene)s with multiple pendant ester groups in various lengths: Synthesis, photophysics and selective hydrolysis . J. Polym. Sci., Part A: Polym. Chem. , 2017 . 55 1880 - 1886 . DOI: 10.1002/pola.v55.11 http://doi.org/10.1002/pola.v55.11 .
Xu, H.; Wu, W.; Chen, Y.; Qiu, T.; Fan, L. J . Construction of response patterns for metal cations by using a fluorescent conjugated polymer sensor array from parallel combinatorial synthesis . ACS Appl. Mater. Interfaces , 2014 . 6 5041 - 5049 . DOI: 10.1021/am5001272 http://doi.org/10.1021/am5001272 .
Pang, Y.; Li, J.; Barton, T. J . Processible poly[( p -phenyleneethynylene)- alt -(2,5-thienyleneethynylene)]s of high luminescence: their synthesis and physical properties . J. Mater. Chem. , 1998 . 8 1687 - 1690 . DOI: 10.1039/a802032i http://doi.org/10.1039/a802032i .
Magde, D.; Wong, R.; Seybold, P. G . Fluorescence quantum yields and their relation to lifetimes of rhodamine 6G and fluorescein in nine solvents: Improved absolute standards for quantum yields . Photochem. Photobiol. , 2002 . 75 327 - 334 . DOI: 10.1562/0031-8655(2002)075<0327:FQYATR>2.0.CO;2 http://doi.org/10.1562/0031-8655(2002)075<0327:FQYATR>2.0.CO;2 .
Beninatto, R.; Borsato, G.; Lucchi, O. D.; Fabris, F.; Lucchini, V.; Zendri, E . New 3,6-bis(biphenyl)diketopyrrolopyrrole dyes and pigments via Suzuki-Miyaura coupling . Dyes Pigments , 2013 . 96 679 - 685 . DOI: 10.1016/j.dyepig.2012.11.011 http://doi.org/10.1016/j.dyepig.2012.11.011 .
Guo, E. Q.; Ren, P. H.; Zhang, Y. L.; Zhang, H. C.; Yang, W. J . Diphenylamine end-capped 1,4-diketo-3,6-diphenylpyrrolo[3,4-c] pyrrole (DPP) derivatives with large two-photon absorption cross-sections and strong two-photon excitation red fluorescence . Chem. Commun. , 2009 . 5859 - 5861 . DOI: 10.1039/b911808j http://doi.org/10.1039/b911808j .
Pedersen, C. J . Cyclic polyethers and their complexes with metal salts . J. Am. Chem. Soc. , 1967 . 89 7017 - 7036 . DOI: 10.1021/ja01002a035 http://doi.org/10.1021/ja01002a035 .
Pliego, J. R . Potassium fluoride activation for the nucleophilic fluorination reaction using 18-crown-6, [2.2.2]-cryptand, pentaethylene glycol and comparison with the new hydro-crown scaffold: A theoretical analysis . Org. Biomol. Chem. , 2018 . 16 3127 - 3137 . DOI: 10.1039/C8OB00418H http://doi.org/10.1039/C8OB00418H .
Misra, R.; Bhattacharyya, S. P. Bhattacharyya, Intramolecular Charge Transfer: Theory and Applications , 1 st edition, 2018 , Wiley-VCH Verlag GmbH & amp;Co. KGaA.
0
浏览量
103
Downloads
0
CSCD
关联资源
相关文章
相关作者
相关机构
京公网安备11010802046900号