A Comparison Study of Physicochemical Properties and Stabilities of H-Shaped Molecule and the Corresponding Polymer

Quan-You Feng; Bin Li; Zong-Yan Zuo; Song-Lin Xie; Meng-Na Yu; Bin Liu; Ying Wei; Ling-Hai Xie; Rui-Dong Xia; Wei Huang

doi:10.1007/s10118-018-2152-5

Your Location：

Home >

Browse articles >

A Comparison Study of Physicochemical Properties and Stabilities of H-Shaped Molecule and the Corresponding Polymer

ARTICLE | Updated：2021-02-18

- A Comparison Study of Physicochemical Properties and Stabilities of H-Shaped Molecule and the Corresponding Polymer
- A Comparison Study of Physicochemical Properties and Stabilities of H-Shaped Molecule and the Corresponding Polymer
- Chinese Journal of Polymer Science 2019年37卷第1期页码：11-17
- Affiliations：
  
  a.Center for Molecular Systems and Organic Devices (CMSOD), Key Laboratory for Organic Electronics and Information Displays & Jiangsu Key Laboratory for Biosensors, Institute of Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing University of Posts & Telecommunications, Nanjing 210023, China
  b.Shaanxi Institute of Flexible Electronics (SIFE), Northwestern Polytechnical University (NPU), Xi’an 710072, China
- Author bio：
  
  iamlhxie@njupt.edu.cn
- Funds：
  
  This work was financially supported by the National Natural Science Foundation of China (Nos. 21504047, 21774061), the Six Peak Talents Foundation of Jiangsu Province (No. XCL-CXTD-009), Natural Science Foundation of Jiangsu Province (No. BK20150834), and Synergetic Innovation Center for Organic Electronics and Information Displays.
- DOI：10.1007/s10118-018-2152-5
  中图分类号：
- 收稿：2018-03-26，
  
  修回：2018-5-4，
  
  录用：2018-5-5，
  
  网络首发：2018-06-01，
  
  纸质出版：2019-01
- Accepted：
Scan QR Code
Citation: Feng, Q. Y.; Li, B.; Zuo, Z. Y.; Xie, S. L.; Yu, M. N.; Liu, B.; Wei, Y.; Xie, L. H.; Xia, R. D.; Huang, W. A comparison study of physicochemical properties and stabilities of H-shaped molecule and the corresponding polymer. Chinese J. Polym. Sci. 2019, 37, 11–17

Quan-You Feng, Bin Li, Zong-Yan Zuo, et al. A Comparison Study of Physicochemical Properties and Stabilities of H-Shaped Molecule and the Corresponding Polymer[J]. Chinese Journal of Polymer Science, 2019, 37(1): 11-17.
Citation: Feng, Q. Y.; Li, B.; Zuo, Z. Y.; Xie, S. L.; Yu, M. N.; Liu, B.; Wei, Y.; Xie, L. H.; Xia, R. D.; Huang, W. A comparison study of physicochemical properties and stabilities of H-shaped molecule and the corresponding polymer. Chinese J. Polym. Sci. 2019, 37, 11–17 DOI： 10.1007/s10118-018-2152-5.

Quan-You Feng, Bin Li, Zong-Yan Zuo, et al. A Comparison Study of Physicochemical Properties and Stabilities of H-Shaped Molecule and the Corresponding Polymer[J]. Chinese Journal of Polymer Science, 2019, 37(1): 11-17. DOI： 10.1007/s10118-018-2152-5.

摘要

Abstract

Rare attention has been paid to the comparison between a monomer and its corresponding polymer in terms of the optoelectronic characteristics. In this article

a model H-shaped molecule and its corresponding polymer

both of which exhibited similar properties including blue emission and solution processing

were designed and synthesized. Optoelectronic properties and various kinds of stability features

including the thermostabilities

spectral stabilities and amplified spontaneous emission characteristic of the monomer and polymer were investigated. In general

the corresponding polymer

exhibited similar optoelectronic properties but deteriorated stabilities compared with its H-shaped monomer

H-1

probably owing to the similar chemical structure but the wider molecular weight distribution and metal catalyst residue. Importantly

monomer

H-1

displayed a comparable ASE threshold value with its polymer

suggesting that H-shaped fluorene-based small molecules may be more promising optical gain media in solid state amplifers and lasers.

关键词

Keywords

references

Xie, L. H.; Yin, C. R.; Lai, W. Y.; Fan, Q. L.; Huang, W . Polyfluorene-based semiconductors combined with various periodic table elements for organic electronics . Prog. Polym. Sci. , 2012 . 37 ( 9 ): 1192 - 1264 . DOI: 10.1016/j.progpolymsci.2012.02.003 http://doi.org/10.1016/j.progpolymsci.2012.02.003 .

Cao, Y.; Zhang, J.; Bai, Y.; Li, R.; Zakeeruddin, S. M.; Grätzel, M. ; Wang, P . Dye-sensitized solar cells with solvent-free ionic liquid electrolytes . J. Phys. Chem. C , 2008 . 112 ( 35 ): 13775 - 13781 . DOI: 10.1021/jp805027v http://doi.org/10.1021/jp805027v .

Feldblyum, J. I.; Mccreery, C. H.; Andrews, S. C.; Kurosawa, T.; Santos, E. J.; Duong, V.; Fang, L.; Ayzner, A. L.; Bao, Z . Few-layer, large-area, 2D covalent organic framework semiconductor thin films . Chem. Commun. , 2015 . 51 ( 73 ): 13894 - 13897 . DOI: 10.1039/C5CC04679C http://doi.org/10.1039/C5CC04679C .

White, M. S.; Kaltenbrunner, M.; Głowacki, E. D.; Gutnichenko, K.; Kettlgruber, G.; Graz, I.; Aazou, S.; Ulbricht, C.; Egbe, D. A. M.; Miron, M. C.; Major, Z.; Scharber, M. C.; Sekitani, T.; Someya, T.; Bauer, S.; Sariciftci, N. S . Ultrathin, highly flexible and stretchable PLEDs . Nat. Photon. , 2013 . 7 ( 10 ): 811 - 816 . DOI: 10.1038/nphoton.2013.188 http://doi.org/10.1038/nphoton.2013.188 .

Sun, M. L.; Zhong, C. M.; Li, F. ; Pei, Q. B . Purified polar polyfluorene for light-emitting diodes and light-emitting electrochemical cells . Chinese J. Polym. Sci. , 2012 . 30 ( 4 ): 503 - 510 . DOI: 10.1007/s10118-012-1132-4 http://doi.org/10.1007/s10118-012-1132-4 .

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 ( 3 ): 897 - 1091 . DOI: 10.1021/cr000013v http://doi.org/10.1021/cr000013v .

Prasad, L. G . Azo dye doped polymer films for nonlinear optical applications . Chinese J. Polym. Sci. , 2014 . 32 ( 5 ): 650 - 657 . DOI: 10.1007/s10118-014-1441-x http://doi.org/10.1007/s10118-014-1441-x .

Ford, E. B.; Lystad, V.; Rasio, F. A . Planet-planet scattering in the upsilon Andromedae system . Nature , 2005 . 434 ( 7035 ): 873 - 876 . DOI: 10.1038/nature03427 http://doi.org/10.1038/nature03427 .

Wei, Q.; Li, Y.; Liu, J. G.; Fang, Q. Y.; Li, J. W.; Yan, X. H.; Xie, L. H.; Qian, Y.; Xia, R. D.; Huang, W . A High performance deep blue organic laser gain material . Adv. Opt. Mater. , 2017 . 5 ( 8 ): 1601003 DOI: 10.1002/adom.201601003 http://doi.org/10.1002/adom.201601003 .

Samuel, I. D. W.; Turnbull, G. A . Organic semiconductor lasers . Chem. Rev. , 2007 . 107 ( 4 ): 1272 - 1295 . DOI: 10.1021/cr050152i http://doi.org/10.1021/cr050152i .

Islam, A.; Liu, Z. Y.; Peng, R. X.; Jiang, W. G.; Lei, T.; Li, W.; Zhang, L.; Yang, R. J.; Guan, Q.; Ge, Z. Y . Furan-containing conjugated polymers for organic solar cells . Chinese J. Polym. Sci. , 2017 . 35 ( 2 ): 171 - 183 . DOI: 10.1007/s10118-017-1886-9 http://doi.org/10.1007/s10118-017-1886-9 .

Brabec, C. J.; Gowrisanker, S.; Halls, J. J.; Laird, D.; Jia, S.; Williams, S. P . Polymer-fullerene bulk-heterojunction solar cells . Adv. Mater. , 2010 . 22 ( 34 ): 3839 - 3856 . DOI: 10.1002/adma.200903697 http://doi.org/10.1002/adma.200903697 .

Guenes, S.; Neugebauer, H.; Sariciftci, N. S . Conjugated polymer-based organic solar cells . Chem. Rev. , 2007 . 107 ( 4 ): 1324 - 1338 . DOI: 10.1021/cr050149z http://doi.org/10.1021/cr050149z .

Sirringhaus, H . Device physics of solution-processed organic field-effect transistors . Adv. Mater. , 2005 . 17 ( 20 ): 2411 - 2425 . DOI: 10.1002/(ISSN)1521-4095 http://doi.org/10.1002/(ISSN)1521-4095 .

Hamadani, B. H.; Natelson, D . Temperature-dependent contact resistances in high-quality polymer field-effect transistors . Appl. Phys. Lett. , 2004 . 84 ( 3 ): 443 - 445 . DOI: 10.1063/1.1639945 http://doi.org/10.1063/1.1639945 .

Yap, B. K.; Xia, R. D.; Campoy-Quiles, M.; Stavrinou, P. N.; Bradley, D. D . Simultaneous optimization of charge-carrier mobility and optical gain in semiconducting polymer films . Nat. Mater. , 2008 . 7 ( 5 ): 376 - 380 . DOI: 10.1038/nmat2165 http://doi.org/10.1038/nmat2165 .

Yu, M. N.; Ou, C. J.; Liu, B.; Lin, D. Q.; Liu, Y. Y.; Xue, W.; Lin, Z. Q.; Lin, J. Y.; Qian, Y.; Wang, S. S.; Cao, H. T.; Bian, L. Y.; Xie, L. H.; Huang, W . Progress in fluorene-based wide-bandgap steric semiconductors . Chinese J. Polym. Sci. , 2017 . 35 ( 2 ): 155 - 170 . DOI: 10.1007/s10118-017-1897-6 http://doi.org/10.1007/s10118-017-1897-6 .

Rabe, T.; Hoping, M.; Schneider, D.; Becker, E.; Johannes, H. H.; Kowalsky, W.; Weimann, T.; Wang, J.; Hinze, P.; Nehls, B. S.; Scherf, U.; Farrell, T. ; Riedl, T . Threshold reduction in polymer lasers based on poly(9,9-dioctylfluorene) with statistical binaphthyl units . Adv. Funct. Mater. , 2005 . 15 ( 7 ): 1188 - 1192 . DOI: 10.1002/(ISSN)1616-3028 http://doi.org/10.1002/(ISSN)1616-3028 .

Kuehne, A. J. C.; Kaiser, M.; Mackintosh, A. R.; Wallikewitz, B. H.; Hertel, D.; Pethrick, R. A.; Meerholz, K . Sub-micrometer patterning of amorphous- and β -phase in a crosslinkable poly(9,9-dioctylfluorene): dual-wavelength lasing from a mixed-morphology device . Adv. Funct. Mater. , 2011 . 21 ( 13 ): 2564 - 2570 . DOI: 10.1002/adfm.201002553 http://doi.org/10.1002/adfm.201002553 .

Grell, M.; Bradley, D. D. C.; Long, X.; Chamberlain, T.; Inbasekaran, M.; Woo, E. P.; Soliman, M . Chain geometry, solution aggregation and enhanced dichroism in the liquid-crystalline conjugated polymer poly(9,9-dioctylfluorene) . Acta Polym. , 1998 . 49 ( 8 ): 439 - 444 . DOI: 10.1002/(ISSN)1521-4044 http://doi.org/10.1002/(ISSN)1521-4044 .

Kuehne, A. J. C.; Mackintosh, A. R.; Pethrick, R. A . β -Phase formation in a crosslinkable poly(9,9-dihexylfluorene) . Polymer , 2011 . 52 ( 24 ): 5538 - 5542 . DOI: 10.1016/j.polymer.2011.09.044 http://doi.org/10.1016/j.polymer.2011.09.044 .

Lin, J. Y.; Zhu, W. S.; Liu, F.; Xie, L. H.; Zhang, L.; Xia, R. D.; Xing, G. C.; Huang, W . A Rational molecular design of β -phase polydiarylfluorenes: synthesis, morphology, and organic lasers . Macromolecules , 2014 . 47 ( 3 ): 1001 - 1007 . DOI: 10.1021/ma402585n http://doi.org/10.1021/ma402585n .

Liu, B.; Lin, J. Y.; Liu, F.; Yu, M. N.; Zhang, X. W.; Xia, R. D.; Yang, T.; Fang, Y. T.; Xie, L. H.; Huang, W . A Highly Crystalline and wide-bandgap polydiarylfluorene with beta-phase conformation toward stable electroluminescence and dual amplified spontaneous emission . ACS Appl. Mater. Interfaces , 2016 . 8 ( 33 ): 21648 - 21655 . DOI: 10.1021/acsami.6b05247 http://doi.org/10.1021/acsami.6b05247 .

Grell, M.; Bradley, D. D. C.; Ungar, G.; Hill, J.; Whitehead, K. S . Interplay of physical structure and photophysics for a liquid crystalline polyfluorene . Macromolecules , 1999 . 32 ( 18 ): 5810 - 5817 . DOI: 10.1021/ma990741o http://doi.org/10.1021/ma990741o .

Knaapila, M.; Torkkeli, M.; Galbrecht, F.; Scherf, U . Crystalline and noncrystalline forms of poly(9,9-diheptylfluorene) . Macromolecules , 2013 . 46 ( 3 ): 836 - 843 . DOI: 10.1021/ma3023124 http://doi.org/10.1021/ma3023124 .

Chen, S. H.; Su, A. C.; Su, C. H.; Chen, S. A . Crystalline forms and emission behavior of poly(9,9-di- n -octyl-2,7-fluorene) . Macromolecules , 2005 . 38 ( 2 ): 379 - 385 . DOI: 10.1021/ma048162t http://doi.org/10.1021/ma048162t .

Tang, R. P.; Tan, Z. A.; Li, Y. F.; Xi, F . Synthesis of new conjugated polyfluorene derivatives bearing triphenylamine moiety through a vinylene bridge and their stable blue electroluminescence . Chem. Mater. , 2006 . 18 ( 4 ): 1053 - 1061 . DOI: 10.1021/cm0522735 http://doi.org/10.1021/cm0522735 .

Setayesh, S.; Grimsdale, A. C.; Weil, T.; Enkelmann, V.; Mullen, K.; Meghdadi, F.; List, E. J. W.; Leising, G . Polyfluorenes with polyphenylene dendron side chains: Toward non-aggregating, light-emitting polymers . J. Am. Chem. Soc. , 2001 . 123 ( 5 ): 946 - 953 . DOI: 10.1021/ja0031220 http://doi.org/10.1021/ja0031220 .

Lee, J.; Cho, H. J.; Jung, B. J.; Cho, N. S.; Shim, H. K . Stabilized blue luminescent polyfluorenes: Introducing polyhedral oligomeric silsesquioxane . Macromolecules , 2004 . 37 ( 23 ): 8523 - 8529 . DOI: 10.1021/ma0497759 http://doi.org/10.1021/ma0497759 .

Jiang, Z.; Liu, Z.; Yang, C.; Zhong, C.; Qin, J.; Yu, G.; Liu, Y . Multifunctional fluorene-based oligomers with novel spiro-annulated triarylamine: Efficient, stable deep-blue electroluminescence, good hole injection, and transporting materials with very high T g . Adv. Funct. Mater. , 2009 . 19 ( 24 ): 3987 - 3995 . DOI: 10.1002/(ISSN)1616-3028 http://doi.org/10.1002/(ISSN)1616-3028 .

Wu, Y. G.; Li, J.; Fu, Y. Q.; Bo, Z. S . Synthesis of extremely stable blue light emitting poly(spirobifluorene)s with suzuki polycondensation . Org. Lett. , 2004 . 6 ( 20 ): 3485 - 3487 . DOI: 10.1021/ol048709o http://doi.org/10.1021/ol048709o .

Kanibolotsky, A. L.; Berridge, R.; Skabara, P. J.; Perepichka, I. F.; Bradley, D. D. C.; Koeberg, M . Synthesis and properties of monodisperse oligofluorene-functionalized truxenes: Highly fluorescent star-shaped architectures . J. Am. Chem. Soc. , 2004 . 126 ( 42 ): 13695 - 13702 . DOI: 10.1021/ja039228n http://doi.org/10.1021/ja039228n .

Zhou, X. H.; Yan, J. C.; Pei, J . Synthesis and relationships between the structures and properties of monodisperse star-shaped oligofluorenes . Org. Lett. , 2003 . 5 ( 19 ): 3543 - 3546 . DOI: 10.1021/ol035461e http://doi.org/10.1021/ol035461e .

Liu, X. M.; Xu, J. W.; Lu, X. H.; He, C. B . Novel glassy tetra( N -alkyl-3-bromocarbazole-6-yl)silanes as building blocks for efficient and nonaggregating blue-light-emitting tetrahedral materials . Org. Lett. , 2005 . 7 ( 14 ): 2829 - 2832 . DOI: 10.1021/ol050687y http://doi.org/10.1021/ol050687y .

Chen, X. W.; Tseng, H. E.; Liao, J. L.; Chen, S. A . Green emission from end-group-enhanced aggregation in polydioetylfluorene . J. Phys. Chem. B , 2005 . 109 ( 37 ): 17496 - 17502 . DOI: 10.1021/jp052549w http://doi.org/10.1021/jp052549w .

Qian, Y.; Wei, Q.; Del Pozo, G.; Mroz, M. M.; Luer, L.; Casado, S.; Cabanillas-Gonzalez, J.; Zhang, Q.; Xie, L.; Xia, R.; Huang, W . H-shaped oligofluorenes for highly air-stable and low-threshold non-doped deep blue lasing . Adv. Mater. , 2014 . 26 ( 18 ): 2937 - 2942 . DOI: 10.1002/adma.v26.18 http://doi.org/10.1002/adma.v26.18 .

Xie, L. H.; Hou, X. Y.; Tang, C.; Hua, Y. R.; Wang, R. J.; Chen, R. F.; Fan, Q. L.; Wang, L. H.; Wei, W.; Peng, B.; Huang, W . Novel H-shaped persistent architecture based on a dispiro building block system . Org. Lett. , 2006 . 8 ( 7 ): 1363 - 1366 . DOI: 10.1021/ol060109x http://doi.org/10.1021/ol060109x .

Zhao, L.; Wang, S. M.; Shao, S. Y.; Ding, J. Q.; Wang, L. X.; Jing, X. B.; Wang, F. S . Stable and efficient deep-blue terfluorenes functionalized with carbazole dendrons for solution-processed organic light-emitting diodes . J. Mater. Chem. C , 2015 . 3 ( 34 ): 8895 - 8903 . DOI: 10.1039/C5TC01711D http://doi.org/10.1039/C5TC01711D .

Li, M.; Tang, S.; Shen, F. Z.; Liu, M. R.; Xie, W. J.; Xia, H.; Liu, L. L.; Tian, L. L.; Xie, Z. Q.; Lu, P.; Hanif, M.; Lu, D.; Cheng, G.; Ma, Y. G . Highly luminescent network films from electrochemical deposition of peripheral carbazole functionalized fluorene oligomer and their applications for light-emitting diodes . Chem. Commun. , 2006 . 3393 - 3395 . DOI: 10.1039/b607242a http://doi.org/10.1039/b607242a .

Ou, C. J.; Ding, X. H.; Li, Y. X.; Zhu, C.; Yu, M. N.; Xie, L. H.; Lin, J. Y.; Xu, C. X.; Huang, W . Conformational effect of polymorphic terfluorene on photophysics, crystal morphologies, and lasing behaviors . J. Phys. Chem. C , 2017 . 121 ( 27 ): 14803 - 14810 . DOI: 10.1021/acs.jpcc.7b03366 http://doi.org/10.1021/acs.jpcc.7b03366 .

Giovanella, U.; Botta, C.; Galeotti, F.; Vercelli, B.; Battiato, S.; Pasini, M . Perfluorinated polymer with unexpectedly efficient deep blue electroluminescence for full-colour OLED displays and light therapy applications . J. Mater. Chem. C , 2013 . 1 ( 34 ): 5322 - 5329 . DOI: 10.1039/c3tc31139b http://doi.org/10.1039/c3tc31139b .

Yu, M. N.; Soleimaninejad, H.; Lin, J. Y.; Zuo, Z. Y.; Liu, B.; Bo, Y. F.; Bai, L. B.; Han, Y. M.; Smith, T. A.; Xu, M.; Wu, X. P.; Dunstan, D. E.; Xia, R. D.; Xie, L. H.; Bradley, D. D. C.; Huang, W . Photophysical and fluorescence anisotropic behavior of polyfluorene β -conformation films . J. Phys. Chem. Lett. , 2018 . 9 ( 2 ): 364 - 372 . DOI: 10.1021/acs.jpclett.7b03148 http://doi.org/10.1021/acs.jpclett.7b03148 .

浏览量

Downloads

CSCD

文章被引用时，请邮件提醒。

Submit

工具集

关联资源

Simplified p-i-n Perovskite Solar Cells with a Multifunctional Polyfullerene Electron Transporter

UV-triggered Polymerization of Polyelectrolyte Composite Coating with Pore Formation and Lubricant Infusion

Solution-processed Molybdenum Oxide Hole Transport Layer Stabilizes Organic Solar Cells

Unfused-ring Acceptors with Dithienobenzotriazole Core for Efficient Organic Solar Cells

Porous Organic Polymers for Photocatalytic Hydrogen Peroxide Production: Recent Advances and Future Perspectives