Effect and Mechanism of Solvent Properties on Solution Behavior and Films Condensed State Structure for the Semi-rigid Conjugated Polymers

Hao Zhang; Tao Li; Bin Liu; Teng-Ning Ma; Long Huang; Ze-Ming Bai; Dan Lu

doi:10.1007/s10118-021-2555-6

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Effect and Mechanism of Solvent Properties on Solution Behavior and Films Condensed State Structure for the Semi-rigid Conjugated Polymers

FEATURE ARTICLE | Updated：2021-03-26

- Effect and Mechanism of Solvent Properties on Solution Behavior and Films Condensed State Structure for the Semi-rigid Conjugated Polymers
- Effect and Mechanism of Solvent Properties on Solution Behavior and Films Condensed State Structure for the Semi-rigid Conjugated Polymers
- Chinese Journal of Polymer Science 2021年39卷第7期页码：796-814
- Affiliations：
  
  State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, China
- Author bio：
  
  lud@jlu.edu.cn
- Funds：
  
  This work is financially supported by the National Natural Science Foundation of China (Nos. 91333103 and 21574053).
- DOI：10.1007/s10118-021-2555-6
  中图分类号：
- 收稿：2020-11-17，
  
  修回：2021-1-2，
  
  录用：2021-1-15，
  
  网络首发：2021-03-26，
  
  纸质出版：2021-05-14
- Accepted：
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Zhang, H.; Li, T.; Liu, B.; Ma, T. N.; Huang, L.; Bai, Z. M.; Lu, D. Effect and mechanism of solvent properties on solution behavior and films condensed state structure for the semi-rigid conjugated polymers. Chinese J. Polym. Sci. 2021, 39, 796–814

Hao Zhang, Tao Li, Bin Liu, et al. Effect and Mechanism of Solvent Properties on Solution Behavior and Films Condensed State Structure for the Semi-rigid Conjugated Polymers[J]. Chinese Journal of Polymer Science, 2021, 39(7): 796-814.
Zhang, H.; Li, T.; Liu, B.; Ma, T. N.; Huang, L.; Bai, Z. M.; Lu, D. Effect and mechanism of solvent properties on solution behavior and films condensed state structure for the semi-rigid conjugated polymers. Chinese J. Polym. Sci. 2021, 39, 796–814 DOI： 10.1007/s10118-021-2555-6.

Hao Zhang, Tao Li, Bin Liu, et al. Effect and Mechanism of Solvent Properties on Solution Behavior and Films Condensed State Structure for the Semi-rigid Conjugated Polymers[J]. Chinese Journal of Polymer Science, 2021, 39(7): 796-814. DOI： 10.1007/s10118-021-2555-6.

摘要

Abstract

Solvents have an essential association with polymer solution behavior. However

few researches have been deeply done on this respect. In recent years

our research group focus on the study on effect of solvent properties on solution behavior and film condensed state structure for semi-rigid conjugated polymer up till to apply for optoelectronic device. Herein

influence of solvent properties including solubility of solvent

aromaticity

polarity and hydrogen bonds on semi-rigid polymer chain solution behavior

i.e.

single chain conformation

chain shape

size and chains aggregated density were studied by means of static/dynamic laser light scattering (DLS/SLS) and exponential law

etc

. Effect of solvent properties on condensed state structure of the semi-rigid conjugated polymer film was studied by UV absorption spectroscopy

PL spectroscopy and electron microscopy

etc

. The essential reasons for the influence were discovered and the mechanism was revealed. It was found that solution behavior with different solvent properties had an essential physical relationship with chains condensed state structure of the semi-rigid conjugated polymers. More importantly

there was a quantitative structure-activity relationship between solution and film. The key to this relationship depended on the interaction between solvent molecules and the semi-rigid conjugated polymer chains. This interaction could also affect optoelectronic devices performance. This study is of great significance to effectively control the condensed state structure of the semi-rigid conjugated polymers in the process of dynamic evolution from solutions to films. It not only enriches the knowledge and understanding of both semi-rigid conjugated polymer solution behaviors and film condensed state physics based on polymer physics

but also is meaningful to practical application for conjugated polymer and other traditional polymer systems.

关键词

Keywords

references

Friend, R. H; Gymer, R. W; Holmes, A. B; Burroughes, J. H; Marks, R. N; Taliani, C; Bradley, D. D. C; Dos Santos, D. A; Bredas, J. L; Logdlund, M; Salaneck, W. R. . Electroluminescence in conjugated polymers . Nature , 1999 . 397 121 - 128 . DOI: 10.1038/16393 http://doi.org/10.1038/16393 .

Brabec, C. J; Sariciftci, N. S; Hummelen, J. C. . Plastic solar cells . Adv. Funct. Mater. , 2001 . 11 15 - 26 . DOI: 10.1002/1616-3028(200102)11:1<15::AID-ADFM15>3.0.CO;2-A http://doi.org/10.1002/1616-3028(200102)11:1<15::AID-ADFM15>3.0.CO;2-A .

Kitagawa, S.; Kitaura, R.; Noro, S. I. . Functional porous coordination polymers . Angew. Chem. Int. Ed. , 2004 . 43 2334 - 2375 . DOI: 10.1002/anie.200300610 http://doi.org/10.1002/anie.200300610 .

Lehn, J. M. . From supramolecular chemistry towards constitutional dynamic chemistry and adaptive chemistry . Chem. Soc. Rev. , 2007 . 36 151 - 160 . DOI: 10.1039/B616752G http://doi.org/10.1039/B616752G .

Zhang, G.; Niu, A.; Peng, S.; Jiang, M.; Tu, Y.; Li, M.; Wu, C. . Formation of novel polymeric nanoparticles . Acc. Chem. Res. , 2001 . 34 249 - 256 . DOI: 10.1021/ar000011x http://doi.org/10.1021/ar000011x .

Beaupre, S; Leclerc, M. . Fluorene-based copolymers for red-light-emitting diodes . Adv. Funct. Mater. , 2002 . 12 192 - 196 . DOI: 10.1002/1616-3028(200203)12:3<192::AID-ADFM192>3.0.CO;2-U http://doi.org/10.1002/1616-3028(200203)12:3<192::AID-ADFM192>3.0.CO;2-U .

Cheng, Y, J; Yang, S. H; Hsu, C. S. . Synthesis of conjugated polymers for organic solar cell applications . Chem. Rev. , 2009 . 109 5868 - 5923 . .

Huang, X; Hu, X. . 15 Major cities' scientific and technological innovation sources are released . China Awards for Science and Technology , 2019 . 6 70 - 72 . .

McGehee, M. D.; Heeger, A. J. . Semiconducting (conjugated) polymers as materials for solid-state lasers . Adv. Mater. , 2000 . 12 1655 - 1668 . DOI: 10.1002/1521-4095(200011)12:22<1655::AID-ADMA1655>3.0.CO;2-2 http://doi.org/10.1002/1521-4095(200011)12:22<1655::AID-ADMA1655>3.0.CO;2-2 .

Pei, J.; Liu, X. L.; Chen, Z. K.; Zhang, X. H.; Lai, Y. H.; Huang, W. . First hydrogen-bonding-induced self-assembled aggregates of a polyfluorene derivative . Macromolecules , 2003 . 36 323 - 327 . DOI: 10.1021/ma020744s http://doi.org/10.1021/ma020744s .

Dudek, S. P.; Pouderoijen, M.; Abbel, R.; Schenning, A. P. H. J.; Meijer, E. W. . Synthesis and energy-transfer properties of hydrogen-bonded oligofluorenes . J. Am. Chem. Soc. , 2005 . 127 11763 - 11768 . DOI: 10.1021/ja052054k http://doi.org/10.1021/ja052054k .

Zaumseil, J; Donley, C. L; Kim, J. S; Friend, R. H; Sirringhaus, H. . Efficient top-gate, ambipolar, light-emitting field-effect transistors based on a green-light-emitting polyfluorene . Adv. Mater. , 2006 . 18 2708 - 2712 . DOI: 10.1002/adma.200601080 http://doi.org/10.1002/adma.200601080 .

Liu, F; Tang, X. Polymer physics (in Chinese), Higher Education Press, Beijing, 2004 , p. 39.

Bhardwaj, N.; Kundu, S. C. . Electrospinning: a fascinating fiber fabrication technique . Biotechnol. Adv. , 2010 . 28 325 - 347 . DOI: 10.1016/j.biotechadv.2010.01.004 http://doi.org/10.1016/j.biotechadv.2010.01.004 .

Kim, J. Y; Lee, K; Coates, N. E; Moses, D; Nguyen, T. Q; Dante, M; Heeger, A. J. . Efficient tandem polymer solar cells fabricated by all-solution processing . Science , 2007 . 317 222 - 225 . DOI: 10.1126/science.1141711 http://doi.org/10.1126/science.1141711 .

Chen, J. W.; Huang, C. C.; Chao, C. Y. . Supramolecular liquid-crystal gels formed by polyfluorene-based π -conjugated polymer for switchable anisotropic scattering device . ACS Appl. Mater. Interfaces , 2014 . 6 6757 - 6764 . DOI: 10.1021/am500518c http://doi.org/10.1021/am500518c .

Raspaud, E.; Lairez, D.; Adam, M.; Carton, J. P. . Triblock copolymers in a selective solvent. 1. Aggregation process in dilute solution . Macromolecules , 1994 . 27 2956 - 2964 . DOI: 10.1021/ma00089a011 http://doi.org/10.1021/ma00089a011 .

Wu, Q. Polymer Condensed Matter Physics (in Chinese), Science Press, Beijing, 2016 , p. 59.

Mes, T; Weegen, R. V. D; Palmans, A. R. A; Meijer, E. W. . Single-chain polymeric nanoparticles by stepwise folding . Angew. Chem. Int. Ed. , 2011 . 50 5085 - 5089 . DOI: 10.1002/anie.201100104 http://doi.org/10.1002/anie.201100104 .

Daoud, M.; Cotton, J. P.; Farnoux, B.; Jannink, G.; Sarma, G.; Benoit, H.; Duplessix, C.; Picot, C.; de Gennes, P. G. . Solutions of flexible polymers Neutron experiments and interpretation . Macromolecules , 1975 . 8 804 - 818 . .

Dai, S.; Tam, K. C.; Jenkins, R. D. . Microstructure of dilute hydrophobically modified alkali soluble emulsion in aqueous salt solution . Macromolecules , 2000 . 33 404 - 411 . DOI: 10.1021/ma990887n http://doi.org/10.1021/ma990887n .

Wang, Z. H.; Lu, Y. Y.; Jin, H.; Luo, C. F.; An, L. J. . Diffusion of a ring threaded on a linear chain . Chinese J. Polym. Sci. , 2020 . 38 1409 - 1417 . DOI: 10.1007/s10118-020-2448-0 http://doi.org/10.1007/s10118-020-2448-0 .

Zhang, X; Dong, H; Hu, W. . Organic semiconductor single crystals for electronics and photonics . Adv. Mater. , 2018 . 1801048 .

Neher, D. . Polyfluorene homopolymers: conjugated liquid-crystalline polymers for bright blue emission and polarized electroluminescence . Macromol. Rapid Commun. , 2001 . 22 1365 - 1385 . DOI: 10.1002/1521-3927(20011101)22:17<1365::AID-MARC1365>3.0.CO;2-B http://doi.org/10.1002/1521-3927(20011101)22:17<1365::AID-MARC1365>3.0.CO;2-B .

Rothe, C; Galbrecht, F; Scherf, U; Monkman, A. . The β -phase of poly(9,9-dioctylfluorene) as a potential system for electrically pumped organic lasing . Adv. Mater. , 2006 . 18 2137 - 2140 . DOI: 10.1002/adma.200600901 http://doi.org/10.1002/adma.200600901 .

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 2564 - 2570 . DOI: 10.1002/adfm.201002553 http://doi.org/10.1002/adfm.201002553 .

Jager, E. W. H.; Smela, E.; Inganas, O. . Microfabricating conjugated polymer actuators . Science , 2000 . 290 1540 - 1545 . DOI: 10.1126/science.290.5496.1540 http://doi.org/10.1126/science.290.5496.1540 .

Huang, L.; Huang, X.; Sun, G.; Gu, C.; Lu, D.; Ma, Y. . Study of β phase and chains aggregation degrees in poly(9,9-dioctylfluorene) (PFO) solution . J. Phys. Chem. C , 2012 . 116 7993 - 7999 . DOI: 10.1021/jp301102t http://doi.org/10.1021/jp301102t .

Li, T.; Huang, L.; Bai, Z.; Li, X.; Liu, B.; Lu, D. . Study on the forming condition and mechanism of the β conformation in poly(9,9-dioctylfluorene) solution . Polymer , 2016 . 88 71 - 78 . DOI: 10.1016/j.polymer.2016.02.015 http://doi.org/10.1016/j.polymer.2016.02.015 .

Bai, Z.; Liu, Y.; Li, T.; Li, X.; Liu, B.; Liu, B.; Lu, D. . Quantitative study on β -phase heredity based on poly(9,9-dioctylfluorene) from solutions to films and the effect on hole mobility . J. Phys. Chem. C , 2016 . 120 27820 - 27828 . DOI: 10.1021/acs.jpcc.6b08941 http://doi.org/10.1021/acs.jpcc.6b08941 .

Liu, B.; Zhang, H.; Ren, J.; Ma, T.; Yu, M.; Xie, L.; Lu, D. . Effect of solvent aromaticity on poly(9,9-dioctylfluorene) (PFO) chain solution behavior and film condensed state structure . Polymer , 2019 . 185 121986 DOI: 10.1016/j.polymer.2019.121986 http://doi.org/10.1016/j.polymer.2019.121986 .

Zhang, H.; Li, T.; Ma, T.; Liu, B.; Ren, J.; Lin, J.; Yu, M.; Xie, L.; Lu, D. . Effect of solvents on the solution state and film condensed state structures of a polyfluorene conjugated polymer in the dynamic evolution process from solution to film . J. Phys. Chem. C , 2019 . 123 27317 - 27326 . DOI: 10.1021/acs.jpcc.9b07288 http://doi.org/10.1021/acs.jpcc.9b07288 .

Ma, T.; Song, N.; Qiu, J.; Zhang, H.; Lu, D. . Synergistic effects of external electric field and solvent vapor annealing with different polarities to enhance β -phase and carrier mobility of the poly(9,9-dioctylfluorene) films . Chem. Res. Chinese Univ. , 2020 . 36 1310 - 1319 . DOI: 10.1007/s40242-020-0129-8 http://doi.org/10.1007/s40242-020-0129-8 .

Knaapila, M.; Dias, F. B.; Garamus, V. M.; Almásy, L.; Torkkeli, M.; Leppänen, K.; Galbrecht, F.; Preis, E.; Burrows, H. D.; Scherf, U.; et al . Influence of side chain length on the self-assembly of hairy-rod poly(9,9-dialkylfluorene)s in the poor solvent methylcyclohexane . Macromolecules , 2007 . 40 9398 - 9405 . DOI: 10.1021/ma0715728 http://doi.org/10.1021/ma0715728 .

Lu, H. H.; Liu, C. Y.; Chang, C. H.; Chen, S. A. . Self-dopant formation in poly(9,9-di- n -octylfluorene) via a dipping method for efficient and stable pure-blue electroluminescence . Adv. Mater. , 2007 . 19 2574 - 2579 . DOI: 10.1002/adma.200602632 http://doi.org/10.1002/adma.200602632 .

Peet, J.; Brocker, E.; Xu, Y.; Bazan, G. C. . Controlled β -phase formation in poly(9,9-di- n -octylfluorene) by processing with alkyl additives . Adv. Mater. , 2008 . 20 1882 - 1885 . DOI: 10.1002/adma.200702515 http://doi.org/10.1002/adma.200702515 .

Zhang, H.; Huang, L.; Li, T.; Liu, B.; Bai, Z.; Li, X.; Lu, D. . Quantitative structure-property relationship of polyfluorene conjugated polymers condensed state from solution to film . Acta Chim. Sin. (in Chinese) , 2019 . 77 397 - 405 . DOI: 10.6023/A19010039 http://doi.org/10.6023/A19010039 .

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 . 49 439 - 444 . DOI: 10.1002/(SICI)1521-4044(199808)49:8<439::AID-APOL439>3.0.CO;2-A http://doi.org/10.1002/(SICI)1521-4044(199808)49:8<439::AID-APOL439>3.0.CO;2-A .

Huang, Z.; Huang, Y.; Li, X.; Zhang, L. . Molecular mass and chain conformations of rhizoma panacis japonici polysaccharides . Carbohydr. Polym. , 2009 . 78 596 - 601 . DOI: 10.1016/j.carbpol.2009.05.027 http://doi.org/10.1016/j.carbpol.2009.05.027 .

Zhang, Y; Li, S; Zhang, L. . Aggregation behavior of triple helical polysaccharide with low molecular weight in diluted aqueous solution . J. Phys. Chem. B , 2010 . 114 4945 - 4954 . DOI: 10.1021/jp9100398 http://doi.org/10.1021/jp9100398 .

Zhang, Y; Wu, Q; Fang, Q; Zhang, Y. X. . A light-scattering study of the aggregation behavior of fluorocarbon-modified polyacrylamides in water . Macromolecules , 1996 . 29 2494 - 2497 . DOI: 10.1021/ma9515792 http://doi.org/10.1021/ma9515792 .

Zheng, Y. Q.; Yao, Z. F.; Lei, T.; Dou, J. H.; Yang, C. Y.; Zou, L.; Meng, X.; Ma, W.; Wang, J. Y.; Pei, J. . Unraveling the solution-state supramolecular structures of donor-acceptor polymers and their influence on solid-state morphology and charge-transport properties . Adv. Mater. , 2017 . 29 1701072 DOI: 10.1002/adma.201701072 http://doi.org/10.1002/adma.201701072 .

Huang, L.; Li, T.; Liu, B.; Zhang, L.; Bai, Z.; Li, X.; Huang, X.; Lu, D. . A transformation process and mechanism between the α -conformation and β -conformation of conjugated polymer PFO in precursor solution . Soft Matter , 2015 . 11 2627 - 2638 . DOI: 10.1039/C5SM00074B http://doi.org/10.1039/C5SM00074B .

Kirkwood, J. G.; Riseman, J. . The intrinsic viscosities and diffusion constants of flexible macromolecules in solution . J. Chem. Phys. , 1948 . 16 565 - 573 . DOI: 10.1063/1.1746947 http://doi.org/10.1063/1.1746947 .

Li, T.; Lu, D. . The shape characteristics of complex single chain and aggregation by exponential law . Acta Chim. Sin. , 2016 . 74 649 - 656 . DOI: 10.6023/A16050252 http://doi.org/10.6023/A16050252 .

Lin, J.; Yu, Z.; Zhu, W.; Xing, G.; Lin, Z.; Yang, S.; Xie, L.; Niu, C.; Huang, W. . A π -conjugated polymer gelator from polyfluorene-based poly(tertiary alcohol) via the hydrogen-bonded supramolecular functionalization . Polym. Chem. , 2013 . 4 477 - 483 . DOI: 10.1039/C2PY20618H http://doi.org/10.1039/C2PY20618H .

Lin, J. Y.; Wong, J.; Xie, L. H.; Dong, X. C.; Yang, H. Y.; Huang, W. . Hydrogen-bonded supramolecular conjugated polymer nanoparticles for white light-emitting devices . Macromol. Rapid Commun. , 2014 . 35 895 - 900 . DOI: 10.1002/marc.201300831 http://doi.org/10.1002/marc.201300831 .

Zeng, G.; Yu, W. L.; Chua, S. J.; Huang, W. . Spectral and thermal spectral stability study for fluorene-based conjugated polymers . Macromolecules , 2002 . 35 6907 - 6914 . DOI: 10.1021/ma020241m http://doi.org/10.1021/ma020241m .

Rodrigues, R. F.; Charas, A.; Morgado, J.; Maçanita, A. . Self-organization and excited-state dynamics of a fluorene-bithiophene copolymer (F8T2) in solution . Macromolecules , 2010 . 43 765 - 771 . DOI: 10.1021/ma902096p http://doi.org/10.1021/ma902096p .

Lee, S. W.; Kim, C. H.; Lee, S. G.; Jeong, J. H.; Choi, J. H.; Lee, E. S. . Mobility improvement of P3HT thin film by high-voltage electrostatic field-assisted crystallization . Electron. Mater. Lett. , 2013 . 9 471 - 476 . DOI: 10.1007/s13391-013-0033-1 http://doi.org/10.1007/s13391-013-0033-1 .

Ren, J.; Li, X.; Ma, T.; Liu, B.; Zhang, H.; Li, T.; Lu, D. . Dynamic evolution from chain disorder to order of PTB7 condensed state structures under external fields . ACS Appl. Mater. Interfaces , 2018 . 10 28093 - 28102 . DOI: 10.1021/acsami.8b08938 http://doi.org/10.1021/acsami.8b08938 .

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