Synthesis of Conjugated Polymers Containing Diketopyrrolopyrrole (DPP) Building Block and the Photophysical Study

Ying-Zhong Wu Yi-Chen Zhang Jia-Jun Chen Li-Juan Fan

Citation:  Ying-Zhong Wu, Yi-Chen Zhang, Jia-Jun Chen, Li-Juan Fan. 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 shu

Synthesis of Conjugated Polymers Containing Diketopyrrolopyrrole (DPP) Building Block and the Photophysical Study

English


    1. [1]

      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

    2. [2]

      Günes, S.; Neugebauer, H.; Sariciftci, N. S. Conjugated polymer-based organic solar cells. Chem. Rev. 2007, 107, 1324-1338. doi: 10.1021/cr050149z

    3. [3]

      Bin, H.; Li, Y. Recent research progress of photovoltaic materials for nonfullerene polymer solar cells. Acta Polymerica Sinica (in Chinese) 2017, 9, 1444-1461. doi: 10.11777/j.issn1000-3304.2017.17119

    4. [4]

      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

    5. [5]

      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

    6. [6]

      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

    7. [7]

      Zhang, E.; Liu, L.; Lv, F.; Wang, S. Water-soluble conjugated polymers for biosensor applications. Acta Polymerica Sinica (in Chinese) 2018, 2, 186-197. doi: 10.11777/j.issn1000-3304.2018.17269

    8. [8]

      McQuade, D. T.; Pullen, A. E.; Swager, T. M. Conjugated polymer-based chemical sensors. Chem. Rev. 2000, 100, 2537-2574. doi: 10.1021/cr9801014

    9. [9]

      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

    10. [10]

      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

    11. [11]

      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

    12. [12]

      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

    13. [13]

      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

    14. [14]

      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

    15. [15]

      Qu, S.; Tian, H. Diketopyrrolopyrrole (DPP)-based materials for organic photovoltaics. Chem. Commun. 2012, 48, 3039-3051. doi: 10.1039/c2cc17886a

    16. [16]

      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, 7, 1082-1096. doi: 10.11777/j.issn1000-3304.2017.17020

    17. [17]

      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

    18. [18]

      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, 2, 295-303. doi: 10.11777/j.issn1000-3304.2018.17253

    19. [19]

      Deng, Y.; Xiao, H.; Qiao, H.; Tan, S. Synthesis and photoelectric performance of conjugated polymers with ullazine unit. Acta Polymerica Sinica (in Chinese) 2017, 6, 922-929. doi: 10.11777/j.issn1000-3304.2017.16314

    20. [20]

      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

    21. [21]

      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

    22. [22]

      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

    23. [23]

      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

    24. [24]

      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

    25. [25]

      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

    26. [26]

      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

    27. [27]

      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(2h,5h)-dione for organic thin-film transistors. J. Polym. Sci., Part A: Polym. Chem. 2012, 50, 2809-2818. doi: 10.1002/pola.26078

    28. [28]

      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

    29. [29]

      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

    30. [30]

      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

    31. [31]

      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

    32. [32]

      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

    33. [33]

      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

    34. [34]

      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

    35. [35]

      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

    36. [36]

      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

    37. [37]

      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

    38. [38]

      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

    39. [39]

      Pedersen, C. J. Cyclic polyethers and their complexes with metal salts. J. Am. Chem. Soc. 1967, 89, 7017-7036. doi: 10.1021/ja01002a035

    40. [40]

      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

    41. [41]

      Misra, R.; Bhattacharyya, S. P. Bhattacharyya, Intramolecular Charge Transfer: Theory and Applications, 1st edition, 2018, Wiley-VCH Verlag GmbH &Co. KGaA.

  • 加载中
计量
  • PDF下载量:  0
  • 文章访问数:  2173
  • HTML全文浏览量:  62
文章相关
  • 发布日期:  2019-11-01
  • 收稿日期:  2019-02-15
  • 修回日期:  2019-02-28
  • 网络出版日期:  2019-04-01
通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索

/

返回文章