Dithienylmaleimide-based D-A Conjugated Polymer Film: Photo-responsive Behavior and Application in Electrical Memory and Logic Gates

Wei Lv; Chun Wang; Xing-Chi Lin; Xiao-Fei Mei; Wen Wang; E Yang; Qi-Dan Ling; Zheng-Huan Lin

doi:10.1007/s10118-021-2594-z

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Dithienylmaleimide-based D-A Conjugated Polymer Film: Photo-responsive Behavior and Application in Electrical Memory and Logic Gates

ARTICLE | Updated：2021-06-15

- Dithienylmaleimide-based D-A Conjugated Polymer Film: Photo-responsive Behavior and Application in Electrical Memory and Logic Gates
- Chinese Journal of Polymer Science Vol. 39, Issue 9, Pages: 1177-1184(2021)
- Affiliations：
  
  a.College of Chemistry and Materials Science, Fujian Normal University, Fuzhou 350007, China
  b.Fujian Provincial Key Laboratory of Polymer Materials, Fujian Normal University, Fuzhou 350007, China
- Author bio：
  
  qdling@fjnu.edu.cn (Q.D.L.)
  zhlin@fjnu.edu.cn (Z.H.L.)
- Funds：
- DOI：10.1007/s10118-021-2594-z
  CLC： M
- Received：10 November 2020，
  
  Revised：2021-4-18，
  
  Accepted：20 April 2021，
  
  Online First：15 June 2021，
  
  Published：18 July 2021
- Accepted：
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Lv, W.; Wang, C.; Lin, X. C.; Mei, X. F.; Wang, W.; Yang, E.; Ling, Q. D.; Lin, Z. H. Dithienylmaleimide-based D-A conjugated polymer film: photo-responsive behavior and application in electrical memory and logic gates. Chinese J. Polym. Sci. 2021, 39, 1177–1184

Wei Lv, Chun Wang, Xing-Chi Lin, et al. Dithienylmaleimide-based D-A Conjugated Polymer Film: Photo-responsive Behavior and Application in Electrical Memory and Logic Gates[J]. Chinese Journal of Polymer Science, 2021, 39(9): 1177-1184.
Lv, W.; Wang, C.; Lin, X. C.; Mei, X. F.; Wang, W.; Yang, E.; Ling, Q. D.; Lin, Z. H. Dithienylmaleimide-based D-A conjugated polymer film: photo-responsive behavior and application in electrical memory and logic gates. Chinese J. Polym. Sci. 2021, 39, 1177–1184 DOI： 10.1007/s10118-021-2594-z.

Wei Lv, Chun Wang, Xing-Chi Lin, et al. Dithienylmaleimide-based D-A Conjugated Polymer Film: Photo-responsive Behavior and Application in Electrical Memory and Logic Gates[J]. Chinese Journal of Polymer Science, 2021, 39(9): 1177-1184. DOI： 10.1007/s10118-021-2594-z.

摘要

Abstract

Solid-stated smart polymers responsive to external stimuli have attracted much attention for potential application in the field of photoelectron devices

logic gates

sensor

data storage and security. However

it is a bigger challenge for polymers than that for small molecules in solid state to acquire stimuli-responsive properties

because polymers with high molecular weight are not as easy to change the packing structure as small molecules under external stimulation. Here

a D-A type alternating copolymer PTMF-o containing 3

4-bisthienylmaleimide (A unit) and fluorene (D unit) is designed and synthesized. Upon irradiation of sunlight

PTMF-o film exhibits a photo-response with the color altering from purple to colorless. It is attributed to the structure of copolymer transformed from ring-opening form (PTMF-o) to ring-closure form (PTMF-c)

resulting from the oxidative photocyclization of 3

4-bisthienylmaleimide unit. Consequently

the ability of charge transfer (CT) from fluorene to 3

4-bisthienylmaleimide unit in PTMF-o can be easily weakened by light stimuli. PTMF-o film displays a WORM-type resistive storage performance for the strong CT. Interestingly

after exposure

the electrical memory behavior

in situ

transfers into FLASH type

due to weak CT in PTMF-c. PTMF-o film can also be employed as smart material to construct NAND and NOR logic gates by using light as input condition. The work provides a simple way to modify the electronic properties of polymers and realize stimuli-response in solid states.

关键词

Keywords

references

Heng, Z.; Shuli, G.; Huimin, K.; Congbin, F.; Gang, L.; Shouzhi, P. . Multi-responsive molecular switch based on a novel photochromic diarylethene derivative bearing a benzocoumarin unit . Tetrahedron , 2020 . 76 130955 DOI: 10.1016/j.tet.2020.130955 http://doi.org/10.1016/j.tet.2020.130955 .

Irie, M. . Diarylethenes for memories and switches . Chem. Rev. , 2000 . 100 1685 - 1716 . DOI: 10.1021/cr980069d http://doi.org/10.1021/cr980069d .

Wurthner, F.; Saha-Moller, C. R.; Fimmel, B.; Ogi, S.; Leowanawat, P.; Schmidt, D. . Perylene bisimide dye assemblies as archetype functional supramolecular materials . Chem. Rev. , 2016 . 116 962 - 1052 . DOI: 10.1021/acs.chemrev.5b00188 http://doi.org/10.1021/acs.chemrev.5b00188 .

Ma, Z.; Wang, Z.; Teng, M.; Xu, Z.; Jia, X. . Mechanically induced multicolor change of luminescent materials . ChemPhysChem , 2015 . 16 1811 - 1828 . DOI: 10.1002/cphc.201500181 http://doi.org/10.1002/cphc.201500181 .

Xia, C. X.; Wang, N.; Sun, P. P.; Tang, S. X.; Xu, X. D.; Tan, Y. B.; Xin, X. . Self-assembly of an alkynylpyrene derivative for multi-responsive fluorescence behavior and photoswitching performance . Soft Matter , 2020 . 16 7390 - 7399 . DOI: 10.1039/D0SM01148G http://doi.org/10.1039/D0SM01148G .

Zhao, H.; Kang, H.; Fan, C.; Liu, G.; Pu, S. . A new multi-functional fluorescent mercuric ion sensor based on diarylethene with triazole-linked rhodamine B unit . Tetrahedron , 2020 . 76 131393 DOI: 10.1016/j.tet.2020.131393 http://doi.org/10.1016/j.tet.2020.131393 .

Calvino, C.; Neumann, L.; Weder, C.; Schrettl, S. . Approaches to polymeric mechanochromic materials . J. Polym. Sci., Part A: Polym. Chem. , 2017 . 55 640 - 652 . DOI: 10.1002/pola.28445 http://doi.org/10.1002/pola.28445 .

Pu, S. Z.; Sun, Q.; Fan, C. B.; Wang, R. J.; Liu, G. . Recent advances in diarylethene-based multi-responsive molecular switches . J. Mater. Chem. C , 2016 . 4 3075 - 3093 . DOI: 10.1039/C6TC00110F http://doi.org/10.1039/C6TC00110F .

Hou, I. C. Y.; Berger, F.; Narita, A.; Müllen, K.; Hecht, S. . Proton-gated ring-closure of a negative photochromic azulene-based diarylethene . Angew. Chem. Int. Ed. , 2020 . 59 18532 - 18536 . DOI: 10.1002/anie.202007989 http://doi.org/10.1002/anie.202007989 .

Abdollahi, A.; Roghani-Mamaqani, H.; Razavi, B.; Salami-Kalajahi, M. . The light-controlling of temperature-responsivity in stimuli-responsive polymers . Polym. Chem. , 2019 . 10 5686 - 5720 . DOI: 10.1039/C9PY00890J http://doi.org/10.1039/C9PY00890J .

Tian, H.; Wang, S. . Photochromic bisthienylethene as multi-function switches . Chem. Commun. , 2007 . 781 - 792 . .

Tian, H.; Feng, Y. . Next step of photochromic switches? . J. Mater. Chem. , 2008 . 18 1617 - 1622 . DOI: 10.1039/b713216f http://doi.org/10.1039/b713216f .

Matsuda, K.; Irie, M. . A diarylethene with two nitronyl nitroxides: photoswitching of intramolecular magnetic interaction . J. Am. Chem. Soc. , 2000 . 122 7195 - 7201 . DOI: 10.1021/ja000605v http://doi.org/10.1021/ja000605v .

Kim, E.; Choi, Y. K.; Lee, M. H. . Photoinduced refractive index change of a photochromic diarylethene polymer . Macromolecules , 1999 . 32 4855 - 4860 . DOI: 10.1021/ma9903409 http://doi.org/10.1021/ma9903409 .

Abdollahi, A.; Mamaqani, H. R.; Razavi, B. . Stimuli-chromism of photoswitches in smart polymers: recent advances and applications as chemosensors . Prog. Polym. Sci. , 2019 . 98 101149 DOI: 10.1016/j.progpolymsci.2019.101149 http://doi.org/10.1016/j.progpolymsci.2019.101149 .

Hunter, A. C.; Moghimi, S. M. . Smart polymers in drug delivery: a biological perspective . Polym. Chem. , 2017 . 8 41 - 51 . DOI: 10.1039/C6PY00676K http://doi.org/10.1039/C6PY00676K .

Kumar, A.; Srivastava, A.; Galaev, I. Y.; Mattiasson, B. . Smart polymers: physical forms and bioengineering applications . Prog. Polym. Sci. , 2007 . 32 1205 - 1237 . DOI: 10.1016/j.progpolymsci.2007.05.003 http://doi.org/10.1016/j.progpolymsci.2007.05.003 .

Zhao, Q.; Wang, Y.; Yan, Y.; Huang, J. . Smart nanocarrier: self-assembly of bacteria-like vesicles with photoswitchable cilia . ACS Nano , 2014 . 8 11341 - 11349 . DOI: 10.1021/nn5042366 http://doi.org/10.1021/nn5042366 .

Zhang, C.; Yao, X.; Wang, J.; Ma, X. . Tunable emission of a tetraphenylethylene copolymer via polymer matrix assisted and aggregation-induced emission . Polym. Chem. , 2017 . 8 4835 - 4841 . DOI: 10.1039/C7PY01013C http://doi.org/10.1039/C7PY01013C .

Zhao, Y.; Liu, Z.; Wang, J.; Chen, Y.; Cui, G.; Xiao, W.; Lin, Z.; Ling, Q. . Highly efficient white electroluminescence from dual-core star-shaped single polymer: performance improved by changing the non-emissive core . J. Mater. Chem. C , 2018 . 6 4318 - 4324 . DOI: 10.1039/C7TC05787C http://doi.org/10.1039/C7TC05787C .

Fleming, C.; Remon, P.; Li, S.; Simeth, N. A.; Konig, B.; Grotli, M.; Andreasson, J. . On the use of diarylmaleimide derivatives in biological contexts: an investigation of the photochromic properties in aqueous solution . Dyes Pigm. , 2017 . 137 410 - 420 . DOI: 10.1016/j.dyepig.2016.10.023 http://doi.org/10.1016/j.dyepig.2016.10.023 .

Yamaguchi, T.; Uchida, K.; Irie, M. . Asymmetric photocyclization of diarylethene derivatives . J. Am. Chem. Soc. , 1997 . 119 6066 - 6071 . DOI: 10.1021/ja970200j http://doi.org/10.1021/ja970200j .

Yamaguchi, T.; Irie, M. . Photochromic properties of diarylethene maleimide derivatives in polar solvents . Chem. Lett. , 2004 . 33 1398 - 1399 . DOI: 10.1246/cl.2004.1398 http://doi.org/10.1246/cl.2004.1398 .

Yamaguchi, T.; Matsuo, M.; Irie, M. . Photochromism of diarylethene maleimide derivatives . B. Chem. Soc. Jpn. , 2005 . 78 1145 - 1148 . DOI: 10.1246/bcsj.78.1145 http://doi.org/10.1246/bcsj.78.1145 .

Ohsumi, M.; Hazama, M.; Fukaminato, T.; Irie, M. . Photocyclization reaction of a diarylmaleimide derivative in polar solvents . Chem. Commun. , 2008 . 3281 - 3283 . .

Falenczyk, C.; Schiedel, M.; Karaman, B.; Rumpf, T.; Kuzmanovic, N.; Grotli, M.; Sippl, W.; Jung, M.; Konig, B. . Chromo-pharmacophores: photochromic diarylmaleimide inhibitors for sirtuins . Chem. Sci. , 2014 . 5 4794 - 4799 . DOI: 10.1039/C4SC01346H http://doi.org/10.1039/C4SC01346H .

Wei, K. X.; Wen, G. X.; Zhao, Y.; Lin, Z. H.; Mei, X. F.; Huang, L. M.; Ling, Q. D. . Diarylmaleimide fluorophores: intensely emissive low-band-gap guest for single white polymers with highly efficient electroluminescence . J. Mater. Chem. C , 2016 . 4 9804 - 9812 . DOI: 10.1039/C6TC03348B http://doi.org/10.1039/C6TC03348B .

Jafarpour, F.; Shamsianpour, M.; Issazadeh, S.; Dorrani, M.; Hazrati, H. . Palladium-catalyzed direct arylation of maleimides: a simple route to bisaryl-substituted maleimides . Tetrahedron , 2017 . 73 1668 - 1672 . DOI: 10.1016/j.tet.2017.01.069 http://doi.org/10.1016/j.tet.2017.01.069 .

Lin, Z.; Mei, X.; Yang, E.; Li, X.; Yao, H.; Wen, G.; Chien, C. T.; Chow, T. J.; Ling, Q. . Polymorphism-dependent fluorescence of bisthienylmaleimide with different responses to mechanical crushing and grinding pressure . CrystEngComm , 2014 . 16 11018 - 11026 . DOI: 10.1039/C4CE00963K http://doi.org/10.1039/C4CE00963K .

Mei, X.; Wen, G.; Wang, J.; Yao, H.; Zhao, Y.; Lin, Z.; Ling, Q. . A Λ-shaped donor- π -acceptor- π -donor molecule with AIEE and CIEE activity and sequential logic gate behaviour . J. Mate. Chem. C , 2015 . 3 7267 - 7271 . DOI: 10.1039/C5TC01314C http://doi.org/10.1039/C5TC01314C .

Zheng, R.; Mei, X.; Lin, Z.; Zhao, Y.; Yao, H.; Lv, W.; Ling, Q. . Strong CIE activity, multi-stimuli-responsive fluorescence and data storage application of new diphenyl maleimide derivatives . J. Mater. Chem. C , 2015 . 3 10242 - 10248 . DOI: 10.1039/C5TC02374B http://doi.org/10.1039/C5TC02374B .

Mei, X.; Wei, K.; Wen, G.; Liu, Z.; Lin, Z.; Zhou, Z.; Huang, L.; Yang, E.; Ling, Q. . Carbazole-based diphenyl maleimides: Multi-functional smart fluorescent materials for data process and sensing for pressure, explosive and pH . Dyes Pigm. , 2016 . 133 345 - 353 . DOI: 10.1016/j.dyepig.2016.06.015 http://doi.org/10.1016/j.dyepig.2016.06.015 .

Mei, X.; Wang, J.; Zhou, Z.; Wu, S.; Huang, L.; Lin, Z.; Ling, Q. . Diarylmaleic anhydrides: unusual organic iuminescence, multi-stimuli response and photochromism . J. Mater. Chem. C , 2017 . 5 2135 - 2141 . DOI: 10.1039/C6TC05519B http://doi.org/10.1039/C6TC05519B .

Ferri, N.; Beccalli, E. M.; Contini, A.; Corsini, A.; Antonino, M.; Radice, T.; Pratesi, G.; Tinelli, S.; Zunino, F.; Gelmi, M. L. . Antiproliferative effects on human tumor cells and rat aortic smooth muscular cells of 2,3-heteroarylmaleimides and heterofused imides . Bioorg. Med. Chem. , 2008 . 16 1691 - 1701 . DOI: 10.1016/j.bmc.2007.11.024 http://doi.org/10.1016/j.bmc.2007.11.024 .

Fields, E. K.; Behrend, S. J. . Diaryl-substituted maleic anhydride . J. Org. Chem. , 1990 . 55 5165 - 5170 . DOI: 10.1021/jo00304a034 http://doi.org/10.1021/jo00304a034 .

Zheng, X.; Wang, J.; Xiao, D.; Chen, H.; Lin, Z.; Ling, Q. . Highly emissive fused diarylmaleimides synthesized by a cascade reaction of selective bromination and visible-light-driven cyclization . Dyes Pigm. , 2021 . 187 .

Qian, C.; Zhao, W. H.; Tian, Y.; Jiang, G. F.; Zhan, T. G.; Zhao, X. . Synthesis, photophysical and electrochemical properties, and self-assembly behavior of two hexaazatriphenylene derivatives: a single bond makes a big difference . Chem. Asian J. , 2016 . 11 839 - 43 . DOI: 10.1002/asia.201600018 http://doi.org/10.1002/asia.201600018 .

Yamamoto, A.; Ohta, E.; Kishigami, N.; Tsukahara, N.; Tomiyori, Y.; Sato, H.; Matsui, Y.; Kano, Y.; Mizuno, K.; Ikeda, H. . Synthesis and basic properties of tetrathieno[2,3-a:3′,2′-c:2″,3″-f:3‴,2‴-h]naphthalene: a new π -conjugated system obtained by photoinduced electrocyclization-dehydrogenation reactions of tetra(3-thienyl)ethene . Tetrahedron Lett. , 2013 . 54 4049 - 4053 . DOI: 10.1016/j.tetlet.2013.05.090 http://doi.org/10.1016/j.tetlet.2013.05.090 .

Wang, F.; Zhang, Y.; Tian, C.; Girit, C.; Zettl, A.; Crommie, M.; Shen, Y. R. . Gate-variable optical transitions in graphene . Science , 2008 . 320 206 - 209 . DOI: 10.1126/science.1152793 http://doi.org/10.1126/science.1152793 .

Erbas-Cakmak, S.; Safacan Kolemen; Sedgwick, A. C.; Gunnlaugsson, T.; James, T. D.; Yoon, J.; Akkaya, E. U. . Molecular logic gates: the past, present and future . Chem. Soc. Rev. , 2018 . 47 2221 - 2510 . DOI: 10.1039/C8CS90037J http://doi.org/10.1039/C8CS90037J .

Andreasson, J.; Pischel, U.; Straight, S. D.; Moore, T. A.; Moore, A. L.; Gust, D. . All-photonic multifunctional molecular logic device . J. Am. Chem. Soc. , 2011 . 133 11641 - 11648 . DOI: 10.1021/ja203456h http://doi.org/10.1021/ja203456h .

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