A Comparison Study of Physicochemical Properties and Stabilities of H-Shaped Molecule and the Corresponding Polymer
- Corresponding author: Ling-Hai Xie, iamlhxie@njupt.edu.cn † These authors contributed equally to this work.
Citation:
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. 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
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
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
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
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. Photonics 2013, 7(10), 811-816.
doi: 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
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
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
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
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
Samuel, I. D. W.; Turnbull, G. A. Organic semiconductor lasers. Chem. Rev. 2007, 107(4), 1272-1295.
doi: 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
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
Guenes, S.; Neugebauer, H.; Sariciftci, N. S. Conjugated polymer-based organic solar cells. Chem. Rev. 2007, 107(4), 1324-1338.
doi: 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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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 Tg. Adv. Funct. Mater. 2009, 19(24), 3987-3995.
doi: 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
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
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
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
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
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
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
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
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
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
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
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
Jingyuan Yang , Xinyu Tian , Liuzhong Yuan , Yu Liu , Yue Wang , Chuandong Dou . Enhancing stability of diradical polycyclic hydrocarbons via P=O-attaching. Chinese Chemical Letters, 2024, 35(8): 109745-. doi: 10.1016/j.cclet.2024.109745
Ting Wang , Xin Yu , Yaqiang Xie . Unlocking stability: Preserving activity of biomimetic catalysts with covalent organic framework cladding. Chinese Chemical Letters, 2024, 35(6): 109320-. doi: 10.1016/j.cclet.2023.109320
Qiyan Wu , Ruixin Zhou , Zhangyi Yao , Tanyuan Wang , Qing Li . Effective approaches for enhancing the stability of ruthenium-based electrocatalysts towards acidic oxygen evolution reaction. Chinese Chemical Letters, 2024, 35(10): 109416-. doi: 10.1016/j.cclet.2023.109416
Xingang Kong , Yabei Su , Cuijuan Xing , Weijie Cheng , Jianfeng Huang , Lifeng Zhang , Haibo Ouyang , Qi Feng . Facile synthesis of porous TiO2/SnO2 nanocomposite as lithium ion battery anode with enhanced cycling stability via nanoconfinement effect. Chinese Chemical Letters, 2024, 35(11): 109428-. doi: 10.1016/j.cclet.2023.109428
Xinpin Pan , Yongjian Cui , Zhe Wang , Bowen Li , Hailong Wang , Jian Hao , Feng Li , Jing Li . Robust chemo-mechanical stability of additives-free SiO2 anode realized by honeycomb nanolattice for high performance Li-ion batteries. Chinese Chemical Letters, 2024, 35(10): 109567-. doi: 10.1016/j.cclet.2024.109567
Hongmei Yu , Baoxi Zhang , Meiju Liu , Cheng Xing , Guorong He , Li Zhang , Ningbo Gong , Yang Lu , Guanhua Du . Theoretical and experimental cocrystal screening of temozolomide with a series of phenolic acids, promising cocrystal coformers. Chinese Chemical Letters, 2024, 35(5): 109032-. doi: 10.1016/j.cclet.2023.109032
Wenxiang Ma , Xinyu He , Tianyi Chen , De-Li Ma , Hongzheng Chen , Chang-Zhi Li . Near-infrared non-fused electron acceptors for efficient organic photovoltaics. Chinese Chemical Letters, 2024, 35(4): 109099-. doi: 10.1016/j.cclet.2023.109099
Liang Ming , Dan Liu , Qiyue Luo , Chaochao Wei , Chen Liu , Ziling Jiang , Zhongkai Wu , Lin Li , Long Zhang , Shijie Cheng , Chuang Yu . Si-doped Li6PS5I with enhanced conductivity enables superior performance for all-solid-state lithium batteries. Chinese Chemical Letters, 2024, 35(10): 109387-. doi: 10.1016/j.cclet.2023.109387
Chenghao Ge , Peng Wang , Pei Yuan , Tai Wu , Rongjun Zhao , Rong Huang , Lin Xie , Yong Hua . Tuning hot carrier transfer dynamics by perovskite surface modification. Chinese Chemical Letters, 2024, 35(10): 109352-. doi: 10.1016/j.cclet.2023.109352
Rui Liu , Yue Yu , Lu Deng , Maoxia Xu , Haorong Ren , Wenjie Luo , Xudong Cai , Zhenyu Li , Jingyu Chen , Hua Yu . The synergistic effect of A-site cation engineering and phase regulation enables efficient and stable Ruddlesden-Popper perovskite solar cells. Chinese Chemical Letters, 2024, 35(12): 109545-. doi: 10.1016/j.cclet.2024.109545
Yan-Kai Zhang , Yong-Zheng Zhang , Chun-Xiao Jia , Fang Wang , Xiuling Zhang , Yuhang Wu , Zhongmin Liu , Hui Hu , Da-Shuai Zhang , Longlong Geng , Jing Xu , Hongliang Huang . A stable Zn-MOF with anthracene-based linker for Cr(VI) photocatalytic reduction under sunlight irradiation. Chinese Chemical Letters, 2024, 35(12): 109756-. doi: 10.1016/j.cclet.2024.109756
Jinqiang Gao , Haifeng Yuan , Xinjuan Du , Feng Dong , Yu Zhou , Shengnan Na , Yanpeng Chen , Mingyu Hu , Mei Hong , Shihe Yang . Methanol steam mediated corrosion engineering towards high-entropy NiFe layered double hydroxide for ultra-stable oxygen evolution. Chinese Chemical Letters, 2025, 36(1): 110232-. doi: 10.1016/j.cclet.2024.110232
Rongjun Zhao , Tai Wu , Yong Hua , Yude Wang . Improving performance of perovskite solar cells enabled by defects passivation and carrier transport dynamics regulation via organic additive. Chinese Chemical Letters, 2025, 36(2): 109587-. doi: 10.1016/j.cclet.2024.109587
Guilong Li , Wenbo Ma , Jialing Zhou , Caiqin Wu , Chenling Yao , Huan Zeng , Jian Wang . A composite hydrogel with porous and homogeneous structure for efficient osmotic energy conversion. Chinese Chemical Letters, 2025, 36(2): 110449-. doi: 10.1016/j.cclet.2024.110449
Shunyu Wang , Yanan Zhu , Yang Zhao , Wanli Nie , Hong Meng . Steric effects and electronic manipulation of multiple donors on S0/S1 transition of Dn-A emitters. Chinese Chemical Letters, 2025, 36(4): 110555-. doi: 10.1016/j.cclet.2024.110555
Xiping Dong , Xuan Wang , Zhixiu Lu , Qinhao Shi , Zhengyi Yang , Xuan Yu , Wuliang Feng , Xingli Zou , Yang Liu , Yufeng Zhao . Construction of Cu-Zn Co-doped layered materials for sodium-ion batteries with high cycle stability. Chinese Chemical Letters, 2024, 35(5): 108605-. doi: 10.1016/j.cclet.2023.108605
Lingjiang Kou , Yong Wang , Jiajia Song , Taotao Ai , Wenhu Li , Mohammad Yeganeh Ghotbi , Panya Wattanapaphawong , Koji Kajiyoshi . Mini review: Strategies for enhancing stability of high-voltage cathode materials in aqueous zinc-ion batteries. Chinese Chemical Letters, 2025, 36(1): 110368-. doi: 10.1016/j.cclet.2024.110368
Jiaxi Xu , Yuan Ma . Influence of Hyperconjugation on the Stability and Stable Conformation of Ethane, Hydrazine, and Hydrogen Peroxide. University Chemistry, 2024, 39(11): 374-377. doi: 10.3866/PKU.DXHX202402049
Hailian Tang , Siyuan Chen , Qiaoyun Liu , Guoyi Bai , Botao Qiao , Fei Liu . Stabilized Rh/hydroxyapatite Catalyst for Furfuryl Alcohol Hydrogenation: Application of Oxidative Strong Metal-Support Interactions in Reducing Conditions. Acta Physico-Chimica Sinica, 2025, 41(4): 100036-. doi: 10.3866/PKU.WHXB202408004
Shitao Fu , Jianming Zhang , Cancan Cao , Zhihui Wang , Chaoran Qin , Jian Zhang , Hui Xiong . Study on the Stability of Purple Cabbage Pigment. University Chemistry, 2024, 39(4): 367-372. doi: 10.3866/PKU.DXHX202401059