Abstract
Solid-state stimuli-responsive materials are attracting increasing attention due to their broad prospects in the field of functional materials, but there are still some challenges. We design and synthesize two efficient solid-state stimuli-responsive materials SP-TPEm (m = 4, 6) based on TPE covalent connection with N-position of spiropyran through different lengths of alkyl spacers. Both of them show aggregation-induced emission behaviors. Efficient solid-state photoswitching between SP-TPEm and their photoisomer MC-TPEm is achieved. Both of the two films show great stimulus-responsive properties, and the characteristic emission peak is at around 460 nm for TPE and 601 nm for MC isomer. Therefore, SP-TPE4 is applied as an anticounterfeiting ink due to its great solid-state photochromic characteristics. In addition, the solid-state films of SP-TPEm are acidochromic responsive. Moreover, the surface wettability of the SP-TPEm films can be adjusted by UV light. Hence, we provide a new strategy for building solid-state multifunctional materials.
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References
Tian H, Yang S (2004) Recent progresses on diarylethene based photochromic switches. ChemSoc Rev 33:85–97
Raymo FM, Tomasulo M (2005) Electron and energy transfer modulation with photochromic switches. Chem Soc Rev 34:327–336
Yu M, Zhang P, Krishnan P, Wang H, Gao Y, Chen S, Zeng R, Cui J, Chen J (2018) From a molecular toolbox to a toolbox for photoswitchable fluorescent polymeric nanoparticles. AdvFunct Mater 28:1804759
Zhang C, Zhou H, Liao L, Feng W, Sun W, Li Z, Xu C, Fang C, Sun L, Zhang Y, Yan C (2010) Luminescence modulation of ordered upconversion nanopatterns by a photochromic diarylethene: rewritable optical storage with nondestructive readout. Adv Mater 22:633–637
Wang Y, Tan X, Zhang Y-M, Zhu S, Zhang I, Yu B, Wang K, Yang B, Li M, Zou B, Zhang SX-A (2014) Dynamic behavior of molecular switches in crystal under pressure and its reflection on tactile sensing. J Am ChemSoc 137:931–939
Garry B, Krongauz V, Weiss V (2000) Spiropyrans and spirooxazines for memories and switches. Chem Rev 100:1741–1754
Kortekaas L, BrowneW R (2019) The evolution of spiropyran: fundamentals and progress of an extraordinarily versatile photochrome. Chem Soc Rev 48:3406–3424
Chi Z, Zhang X, Xu B, Zhou X, Ma C, Zhang Y, Liu S, Xu J (2012) Recent advances in organic mechanofluorochromic materials. Chem Soc Rev 41:3878–3896
Klajn R (2014) Spiropyran-based dynamic materials. Chem Soc Rev 43:148–184
Li M, Zhang Q, Zhou YN, Zhu SP (2018) Let spiropyran help polymers feel force! Prog Polym Sci 79:26–39
Pugachev AD, Ozhogina IV, Lukyanova MB, Lukyanov BS, Rostovtseva IA, Dorogan IV, Makarova NI, Tkachev VV, Metelitsa AV, Aldoshin SM (2020) Visible to near-IR molecular switches based on photochromic indoline spiropyrans with a conjugated cationic fragment. Spectrochim Acta A 230:118041
Zhang R, Hu L, Xu Z, Song Y, Li H, Zhang X, Gao X, Wang M, Xian C (2020) A highly selective probe for fluorescence turn-on detection of Fe3+ ion based on a novel spiropyran derivative. J Mol Struct 1204:127481
Harada J, Kawazoe Y, Ogawa K (2010) Photochromism of spiropyrans and spirooxazines in the solid state: low temperature enhances photocoloration. Chem Commun 46:2593–2595
Qi Q, Li C, Liu X, Jiang S, Xu Z, Lee R, Zhu M, Xu B, Tian W (2017) Solid-state photoinduced luminescence switch for advanced anticounterfeiting and super-resolution imaging applications. J Am Chem Soc 139:16036–16039
Su X, Yu Q, Zhang T, Zhang Y, Yu L, Zhang L, Li M, Liu Y, Zhang SXA (2016) Fluorescence molecular switch with high contrast multi-emissions and on/off states. RSC Adv 6:90305–90309
Wu Z, Pan K, Mo S, Wang B, Zhao X, Yin M (2018) Tetraphenylethene-induced free volumes for the isomerization of spiropyran toward multifunctional materials in the solid state. ACS Appl Mater Interfaces 10:30879–30886
Zhao Q, Zhang X, Wei Q, Wang J, Shen X, Qin A, Sun J, Tang BZ (2012) Tetraphenylethene modified perylene bisimide: effect of the number of substituents on AIE performance. Chem Commun 48:11671–11673
Mei J, Leung N, Kwok R, Lam J, Tang BZ (2015) Aggregation-induced emission: together we shine United We Soar. Chem Rev 115:11718–11940
Qi Q, Qian J, Ma S, Xu B, Zhang S, Tian W (2015) Reversible multistimuli-response fluorescent switch based on tetraphenylethene-spiropyran molecules. Chem - Eur J 21:1149–1155
Yang Z, Qin W, Leung NLC, Arseneault M, Lam JWY, Liang G, Sung HHY, Williams ID, Tang BZ (2016) A mechanistic study of AIE processes of TPE luminogens: intramolecular rotation vs. configurational isomerization. J Mater Chem C 4:99–107
Dang D, Qiu Z, Han T, Liu Y, Chen M, Kwok RTK, Lam JWY, Tang BZ (2018) 1 + 1 >> 2: dramatically enhancing the emission efficiency of TPE-Based AIEgens but keeping their emission color through tailored alkyl linkages. Adv Funct Mater 28:1707210
Qi Q, Qian J, Tan X, Zhang J, Wang L, Xu B, Zou B, Tian W (2015) Remarkable turn-on and color-tuned piezochromic luminescence: mechanically switching intramolecular charge transfer in molecular crystals. Adv Funct Mater 25:4005–4010
Shi J, Chang N, Li C, Mei J, Deng C, Luo X, Liu Z, Bo Z, Dong YQ, Tang BZ (2012) Locking the phenyl rings of tetraphenylethene step by step: understanding the mechanism of aggregation-induced emission. Chem Commun 48:10675–10677
Xie Y, Tu J, Zhang T, Wang J, Xie Z, Chi Z, Peng Q, Li Z (2017) Mechanoluminescence from pure hydrocarbon AIEgen. Chem Commun 53:11330–11333
Peng HQ, Zheng X, Han T, Kwok RTK, Lam JWY, Huang X, Tang BZ (2017) Dramatic differences in aggregation-induced emission and supramolecular polymerizability of tetraphenylethene-based stereoisomers. J Am Chem Soc 139:10150–10156
Huang L, Qiu Y, Wu C, Ma Z, Shen Z, Jia X (2018) A multi-state fluorescent switch with multifunction of AIE, methanol-responsiveness, photochromism and mechanochromism. J Mater Chem C6:10250–10255
O’Bryan G, Wong BM, McElhanon JR (2010) Stress sensing in polycaprolactone films via an embedded photochromic compound. ACS Appl Mater Interfaces 2(6):1594–1600
Guo Y, Shi D, Luo Z, Xu J, Li M, Yang L, Yu Z, Chen E, Xie H (2017) High efficiency luminescent liquid crystalline polymers based on aggregation-induced emission and “Jacketing” effect: design synthesis, photophysical property, and phase structure. Macromolecules 50:9607–9616
Kundu PK, Olsen G, Kiss V, Klajn R (2014) Nanoporous frameworks exhibiting multiple stimuli responsiveness. Nat Commun 5:3588
Acknowledgements
This work was supported by the National Natural Science Foundation of China (NNSFS 51503174), the Natural Science Foundation of Hunan Province (NSFH 2018JJ3499) and the Education Department of Hunan Province (No. 18C0120).
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Wu, L., Chen, R., Luo, Z. et al. Solid-state photochromism and acidochromism multifunctional materials constructed by tetraphenylethene and spiropyran. J Mater Sci 55, 12826–12835 (2020). https://doi.org/10.1007/s10853-020-04930-x
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DOI: https://doi.org/10.1007/s10853-020-04930-x