Advertisement

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

  • Ying-Zhong Wu
  • Yi-Chen Zhang
  • Jia-Jun Chen
  • Li-Juan FanEmail author
Article
  • 13 Downloads

Abstract

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 redshift was observed. Discussion about the structure-property relationships was carried out in detail.

Keywords

Conjugated polymer Diketopyrrolopyrrole Building block Sonogashira coupling Photophysics 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Notes

Acknowledgments

This work was financially supported by the Natural Science Foundation of Jiangsu Higher Education Institutions (No. 18KJA430014), the Natural Science Foundation of Jiangsu Province (No. BK20181441), and the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD).

Supplementary material

10118_2019_2248_MOESM1_ESM.pdf (717 kb)
Synthesis of Conjugated Polymers Containing Diketopyrrolopyrrole (DPP) Building Block and the Photophysical Study

References

  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.CrossRefGoogle Scholar
  2. 2.
    Günes, S.; Neugebauer, H.; Sariciftci, N. S. Conjugated polymer-based organic solar cells. Chem. Rev. 2007, 107, 1324–1338.CrossRefGoogle Scholar
  3. 3.
    Bin, H.; Li, Y. Recent research progress of photovoltaic materials for nonfullerene polymer solar cells. Acta Polymerica Sinica (in Chinese) 2017, 1444–1461.Google Scholar
  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.CrossRefGoogle Scholar
  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.CrossRefGoogle Scholar
  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.CrossRefGoogle Scholar
  7. 7.
    Zhang, E.; Liu, L.; Lv, F.; Wang, S. Water-soluble conjugated polymers for biosensor applications. Acta Polymerica Sinica (in Chinese) 2018, 186–197.Google Scholar
  8. 8.
    McQuade, D. T.; Pullen, A. E.; Swager, T. M. Conjugated polymer-based chemical sensors. Chem. Rev. 2000, 100, 2537–2574.CrossRefGoogle Scholar
  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.CrossRefGoogle Scholar
  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.CrossRefGoogle Scholar
  11. 11.
    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.CrossRefGoogle Scholar
  12. 12.
    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.CrossRefGoogle Scholar
  13. 13.
    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.CrossRefGoogle Scholar
  14. 14.
    Qu, S.; Tian, H. Diketopyrrolopyrrole (DPP)-based materials for organic photovoltaics. Chem. Commun. 2012, 48, 3039–3051.CrossRefGoogle Scholar
  15. 15.
    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.Google Scholar
  16. 16.
    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.CrossRefGoogle Scholar
  17. 17.
    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.Google Scholar
  18. 18.
    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.Google Scholar
  19. 19.
    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.CrossRefGoogle Scholar
  20. 20.
    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.CrossRefGoogle Scholar
  21. 21.
    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.CrossRefGoogle Scholar
  22. 22.
    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.CrossRefGoogle Scholar
  23. 23.
    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.CrossRefGoogle Scholar
  24. 24.
    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.CrossRefGoogle Scholar
  25. 25.
    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.CrossRefGoogle Scholar
  26. 26.
    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.CrossRefGoogle Scholar
  27. 27.
    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.CrossRefGoogle Scholar
  28. 28.
    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.CrossRefGoogle Scholar
  29. 29.
    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.CrossRefGoogle Scholar
  30. 30.
    Zhao, Y. J.; Miao, K.; Zhu, Z.; Fan, L. J. Fluorescence quenching of a conjugated polymer by synergistic amine-carboxylic acid and p-p interactions for selective detection of aromatic amines in aqueous solution. ACS Sens. 2017, 2, 842–847.CrossRefGoogle Scholar
  31. 31.
    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.CrossRefGoogle Scholar
  32. 32.
    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.CrossRefGoogle Scholar
  33. 33.
    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.CrossRefGoogle Scholar
  34. 34.
    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.CrossRefGoogle Scholar
  35. 35.
    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.CrossRefGoogle Scholar
  36. 36.
    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.CrossRefGoogle Scholar
  37. 37.
    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.Google Scholar
  38. 38.
    Pedersen, C. J. Cyclic polyethers and their complexes with metal salts. J. Am. Chem. Soc. 1967, 89, 7017–7036.CrossRefGoogle Scholar
  39. 39.
    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 hydrocrown scaffold: A theoretical analysis. Org. Biomol. Chem. 2018, 16, 3127–3137.CrossRefGoogle Scholar
  40. 40.
    Misra, R.; Bhattacharyya, S. P. Bhattacharyya, Intramolecular Charge Transfer: Theory and Applications, 1st edition, 2018, Wiley-VCH Verlag GmbH & Co. KGaA.CrossRefGoogle Scholar

Copyright information

© Chinese Chemical Society Institute of Chemistry, Chinese Academy of Sciences Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  • Ying-Zhong Wu
    • 1
  • Yi-Chen Zhang
    • 1
  • Jia-Jun Chen
    • 1
  • Li-Juan Fan
    • 1
    Email author
  1. 1.Department of Polymer Science and Engineering, College of Chemistry, Chemical Engineering and Materials ScienceSoochow UniversitySuzhou, JiangsuChina

Personalised recommendations