光响应型分子的合成及应用研究进展
收稿日期: 2022-04-18
网络出版日期: 2022-11-03
基金资助
国家自然科学基金项目(21878180);国家自然科学基金项目(21908137);国家自然科学基金项目(U20A20149);青海省重点研发与转化计划项目(2020-GX-101);山西省应用基础研究计划项目(201901D211180);山西省回国留学人员科研项目(HGKY2019005)
Research progress on synthesis and application of photoresponsive molecules
Received date: 2022-04-18
Online published: 2022-11-03
张飞宇 , 李恩泽 , 王鑫 , 成怀刚 , 程芳琴 . 光响应型分子的合成及应用研究进展[J]. 无机盐工业, 2022 , 54(10) : 68 -78 . DOI: 10.19964/j.issn.1006-4990.2022-0214
As a kind of stimuli-responsive molecules,light-responsive molecules have been widely used in smart materials,light-controlled devices and other fields due to their advantages of signal stability,remote control,transient and environmental protection.Among them,the most typical and widely studied are photoisomeric molecules.The structure of photoisomeric molecules change under specific wavelengths of light,sometimes with macroscopic color changing.Under another wavelength of light,the structure reverts back to their original structure and the color fade.The synthesis and preparation of spiropyran,azobenzene,diaryl ethylene and other mainstream photoisomeric molecules,the light response mechanism and their applications in practical production and life such as salt lake resource extraction,drug detection and energy storage material preparation were reviewed.The development trends of photoresponsive molecules in low-cost and environment-friendly synthesis,composite functional materials,intelligent molecular devices and so on were prospected.
| [1] | DECKER H, FELSER H.über cyclische oxoniumsalze aus dicumarketon und über spiropyranderivate[J].European Journal of Inorganic Chemistry, 2010, 41(2): 2997-3007. |
| [2] | BERKOVIC G, KRONGAUZ V, WEISS V.Spiropyrans and spirooxazines for memories and switches[J].Chemical Reviews, 2000, 100(5): 1741-1754. |
| [3] | KORTEKAAS L, BROWNE W R.The evolution of spiropyran:Fundamentals and progress of an extraordinarily versatile photochrome[J].Chemical Society Reviews, 2019, 48(12): 3406-3424. |
| [4] | CHI Zhenguo, ZHANG Xiqi, XU Bingjia, et al.Recent advances in organic mechanofluorochromic materials[J].Chemical Society Reviews, 2012, 41(10): 3878-3896. |
| [5] | KLAJN R.Spiropyran-based dynamic materials[J].Chemical Society Reviews, 2014, 43(1): 148-184. |
| [6] | LI Meng, ZHANG Qi, ZHOU Yinning, et al.Let spiropyran help polymers feel force![J].Progress in Polymer Science, 2018, 79: 26-39. |
| [7] | 张婷.螺吡喃化合物在不同介质中的光致变色行为及光响应机理研究[D].广州:广东工业大学, 2016. |
| [7] | ZHANG Ting.Photochromic behavior and light response mechanism of spiropyran compounds in different media [D].Guangzhou:Guangdong University of Technology, 2016. |
| [8] | 伍亮.含螺吡喃化合物的合成、表征及其刺激响应特性研究[D].湘潭:湘潭大学, 2020. |
| [8] | WU Liang.Synthesis,characterization and stimulus responsive characteristics of compounds containing spiropyran groups[D].Xiangtan:Xiangtan University, 2020. |
| [9] | LI Xiaoliu, LI Jinliang, WANG Yongmei, et al.Synthesis of functionalized spiropyran and spirooxazine derivatives and their photochromic properties[J].Journal of Photochemistry and Photobiology A:Chemistry, 2004, 161(2/3): 201-213. |
| [10] | DAY J H.Thermochromism[J].Chemical Reviews, 1963, 63(1): 65-80. |
| [11] | SCHANZE K S.Photochemistry of organic molecules in isotropic and anisotropic media[M].Boca Raton:CRC Press, 2003: 309. |
| [12] | BAHR J L, KODIS G, DE LA GARZA L, et al.Photoswitched singlet energy transfer in a porphyrin-spiropyran dyad[J].Journal of the American Chemical Society, 2001, 123(29): 7124-7133. |
| [13] | FISHER E, HIRSHBERG Y.Formation of coloured forms of spiropyrans by low-temperature[J].Journal of the Chemical Society, 1952, 11: 4522-4524. |
| [14] | FLOREA L, WAGNER K, WAGNER P, et al.Photo-chemopropulsion:Light-stimulated movement of microdroplets[J].Advan-ced Materials:Deerfield Beach,Fla., 2014, 26(43): 7339-7345. |
| [15] | SUMARU K, KAMEDA M, KANAMORI T, et al.Reversible and efficient proton dissociation of spirobenzopyran-functionalized poly(N-isopropylacrylamide) in aqueous solution triggered by light irradiation and temporary temperature rise[J].Macromolecules, 2004, 37(21): 7854-7856. |
| [16] | STUMPEL J E, LIU Danqing, BROER D J, et al.Photoswitchable hydrogel surface topographies by polymerisation-induced diffusion[J].Chemistry:Weinheim an Der Bergstrasse,Germany, 2013, 19(33): 10922-10927. |
| [17] | XIE Xiaojiang, CRESPO G A, MISTLBERGER G, et al.Photocurrent generation based on a light-driven proton pump in an artificial liquid membrane[J].Nature Chemistry, 2014, 6(3): 202-207 |
| [18] | SAKAMOTO H, YOKOHATA T, YAMAMURA T, et al.Liquid-liquid extraction of alkali metal ions with photochromic crowned spirobenzopyrans[J].Analytical Chemistry, 2002, 74(11): 2522-2528. |
| [19] | KATAYAMA Y, NITA K, UEDA M, et al.Synthesis of chromogenic crown ethers and liquid-liquid extraction of alkali metal ions[J].Analytica Chimica Acta, 1985, 173: 193-209. |
| [20] | LI Enze, KANG Jin, YE Peiyuan, et al.A prospective material for the highly selective extraction of lithium ions based on a photochromic crowned spirobenzopyran[J].Journal of Materials Chemistry.B, 2019, 7(6): 903-907. |
| [21] | NA J H, PARK S C, SOHN Y, et al.Realizing the concept of a scalable artificial iris with self-regulating capability by reversible photoreaction of spiropyran dyes[J].Biomaterials, 2013, 34(13): 3159-3164. |
| [22] | BARMAN S,DAS J, BISWAS S, et al.A spiropyran-coumarin platform:An environment sensitive photoresponsive drug delivery system for efficient cancer therapy[J].Journal of Materials Chemistry.B, 2017, 5(21): 3940-3944. |
| [23] | KANG Jin, LI Enze, CUI Li, et al.Lithium ion specific fluorescent reversible extraction-release based on spiropyran isomerization combining crown ether coordination and its bioimaging[J].Sensors and Actuators B:Chemical, 2021,327.Doi:10.1016/j.snb.2020.128941 . |
| [24] | ZHANG Weijie, HUO Fangjun, YUE Yongkang, et al.Heat stroke in cell tissues related to sulfur dioxide level is precisely monitored by light-controlled fluorescent probes[J].Journal of the American Chemical Society, 2020, 142(6): 3262-3268. |
| [25] | EOM T, KHAN A.Push-pull azobenzene chromophores with nega-tive halochromism[J].Dyes and Pigments, 2021,188.Doi:10.1016/j.dyepig.2021.109197. |
| [26] | ORLIKOWSKA H, SOBOLEWSKA A, BARTKIEWICZ S.Light-responsive surfactants:Photochromic properties of water-soluble azobenzene derivatives[J].Journal of Molecular Liquids, 2020,316.Doi:10.1016/j.molliq.2020.113842 . |
| [27] | NATANSOHN A, ROCHON P.Photoinduced motions in azo-containing polymers[J].Chemical Reviews, 2002, 102(11): 4139-4175. |
| [28] | 于春燕.偶氮苯类光响应薄膜的制备及其性能研究[D].青岛:青岛科技大学, 2020. |
| [28] | YU Chunyan.Preparation and properties study of azobenzene-based photoresponsive films[D].Qingdao:Qingdao University of Science & Technology, 2020. |
| [29] | WEN Yongqiang, YI Wenhui, MENG Lingjie, et al.Photochemi-cal-controlled switching based on azobenzene monolayer modified silicon(111) surface[J].The Journal of Physical Chemistry.B, 2005, 109(30): 14465-14468. |
| [30] | CRECCA C R, ROITBERG A E.Theoretical study of the isomerization mechanism of azobenzene and disubstituted azobenzene derivatives[J].The Journal of Physical Chemistry.A, 2006, 110(26): 8188-8203. |
| [31] | MAGEE J L, SHAND W, EYRING H.Non-adiabatic reactions.Rotation about the double bond[J].Journal of the American Che- mical Society, 1941, 63(3): 677-688. |
| [32] | CURTIN D Y, GRUBBS E J, MCCARTY C G.Uncatalyzed syn-anti isomerization of imines,oxime ethers,and haloimines1 [J].Journal of the American Chemical Society, 1966, 88(12): 2775-2786. |
| [33] | LI Zhiyong, WANG Huiyong, CHU Mengen, et al.Photo-isomerization and light-modulated aggregation behavior of azobenzene-based ionic liquids in aqueous solutions[J].RSC Advances, 2017, 7(71): 44688-44695. |
| [34] | LI Zhiyong, YUAN Xiaoqing, FENG Ying, et al.A reversible conductivity modulation of azobenzene-based ionic liquids in aqueous solutions using UV/vis light[J].Physical Chemistry Chemical Physics:PCCP, 2018, 20(18): 12808-12816. |
| [35] | 李金星.几种偶氮苯衍生物的合成及其光学性质[D].开封:河南大学, 2020. |
| [35] | LI Jinxing.Synthesis and optical properties of several azobenzene derivatives[D].Kaifeng:Henan University, 2020. |
| [36] | BONACCHI S, CANTELLI A, BATTISTELLI G, et al.Photoswitchable NIR-emitting gold nanoparticles[J].Angewandte Che-mie:International Ed.in English, 2016, 55(37): 11064-11068. |
| [37] | 张雪花, 王倩, 胡芳仁.掺偶氮苯二氧化钛基复合薄膜的制备及光开关性能[J].硅酸盐学报, 2021, 49(3): 537-543. |
| [37] | ZHANG Xuehua, WANG Qian, HU Fangren.Preparation and optical switching properties of titanium dioxide based hybrid films doped with azobenzene[J].Journal of the Chinese Ceramic Society, 2021, 49(3): 537-543. |
| [38] | 张鹏.光响应偶氮苯复合材料及其聚合物的光致形变研究[D].北京:北京科技大学, 2022. |
| [38] | ZHANG Peng.Photoinduced deformation of photoresponsive azobenzene-based composites and polymers[D].Beijing:University of Science and Technology Beijing, 2022. |
| [39] | MA Yi, WANG Xiuli, JIA Yushuai, et al.Titanium dioxide-based nanomaterials for photocatalytic fuel generations[J].Chemical Reviews, 2014, 114(19): 9987-10043. |
| [40] | XU Xingtang, WU Bo, ZHANG Peng, et al.Molecular solar thermal storage enhanced by hyperbranched structures[J].Solar RRL, 2020, 4(1).Doi:10.1002/solr.201900422 . |
| [41] | HAN G G D, LI Huashan, GROSSMAN J C.Optically-controlled long-term storage and release of thermal energy in phase-change materials[J].Nature Communications, 2017, 8(1): 1-10. |
| [42] | IRIE M, MOHRI M.Thermally irreversible photochromic systems.Reversible photocyclization of diarylethene derivatives[J].The Journal of Organic Chemistry, 1988, 53(4): 803-808. |
| [43] | TAKAMI S, KOBATAKE S, KAWAI T, et al.Extraordinarily high thermal stability of the closed-ring isomer of 1,2-bis(5-methyl-2-phenylthiazol-4-yl)perfluorocyclopentene[J].Chemistry Letters, 2003, 32(10): 892-893. |
| [44] | 王云.新型含氰基二芳基乙烯的合成和性质研究[D].西安:西安理工大学, 2014. |
| [44] | WANG Yun.Synthesis and properties of a novel photochromic diarylethene with 4-cyanophenyl groups[D].Xi'an:Xi'an University of Technology, 2014. |
| [45] | 郭妮.二芳基乙烯和螺吡喃化合物的光化学反应机理研究[D].西安:陕西师范大学, 2018. |
| [45] | GUO Ni. Study on photochemical reaction mechanism of diaryl ethylene and spiropyran compounds[D].Xi'an:Shaanxi Normal University, 2018. |
| [46] | FUKUMOTO S, NAKASHIMA T, KAWAI T.Photon-quantitative reaction of a dithiazolylarylene in solution[J].Angewandte Chemie, 2011, 123(7): 1603-1606. |
| [47] | 王聪敏, 潘桂兰, 赵利华, 等. 有机光致变色材料的最新成就与机遇[J].有机化学, 2001, 21(11): 954-961. |
| [47] | WANG Congmin, PAN Guilan, ZHAO Lihua, et al.Advances and prospects of organic photochromics[J].Chinese Journal of Organic Chemistry, 2001, 21(11): 954-961. |
| [48] | 李萌祺, 张志鹏, 朱为宏.位阻和电子效应对位阻型二芳基乙烯光响应性能的影响[J].华东理工大学学报:自然科学版, 2020, 46(5): 642-652. |
| [48] | LI Mengqi, ZHANG Zhipeng, ZHU Weihong.Steric and electronic effects on the light-responsive performance of sterically-hindered diarylethenes[J].Journal of East China University of Science and Technology, 2020, 46(5): 642-652. |
| [49] | ICHIKAWA T, MORIMOTO M, IRIE M.Diastereoselective photocyclization of a photochromic diarylethene having a benzo[b]phosphole P-oxide group[J].Dyes and Pigments, 2017, 137: 214-220. |
| [50] | STELLACCI F, TOSCANO F, GALLAZZI M C, et al.From a photochromic diarylethene monomer to a dopable photochromic polymer:Optical properties[J].Synthetic Metals, 1999, 102(1/2/3): 979-980. |
| [51] | JEONG Y, YANG S I, KIM E, et al.A high-content diarylethene photochromic polymer for an efficient fluorescence modulation[J].Macromolecular Rapid Communications, 2006, 27: 1769-1773. |
| [52] | WU Huang, CHEN Yong, LIU Yu.Reversibly photoswitchable supramolecular assembly and its application as a photoerasable fluorescent ink[J].Advanced Materials:Deerfield Beach,Fla., 2017, 29(10).Doi: 10.1002/adma.201605271 . |
| [53] | LIU Guoxing, ZHANG Yingming, ZHANG Lu, et al.Controlled photoerasable fluorescent behaviors with dithienylethene-based molecular turnstile[J].ACS Applied Materials & Interfaces, 2018, 10(15): 12135-12140. |
| [54] | 余茂林.基于二芳基乙烯的光开关聚合物材料的合成与应用[D].湘潭:湘潭大学, 2019. |
| [54] | YU Maolin.Synthesis and application of diarylethene-based photoswitchable polymeric materials[D].Xiangtan:Xiangtan University, 2019. |
| [55] | JIANG Guiyuan, WANG Sheng, YUAN Wenfang, et al.Highly fluorescent contrast for rewritable optical storage based on photochromic bisthienylethene-bridged naphthalimide dimer[J].Che- mistry of Materials, 2006, 18(2): 235-237. |
| [56] | LI Heng, WANG Jingxia, LIN Hui, et al.Amplification of fluorescent contrast by photonic crystals in optical storage[J].Advanced Materials:Deerfield Beach,Fla., 2010, 22(11): 1237-1241. |
| [57] | 王迎辉, 陈元涛, 张炜, 等. 香草醛类席夫碱的制备及其对水中碘的吸附研究[J].环境科学学报, 2021, 41(10): 4013-4021. |
| [57] | WANG Yinghui, CHEN Yuantao, ZHANG Wei, et al.Preparation of vanillin Schiff base and its adsorption of iodine in water[J].Acta Scientiae Circumstantiae, 2021, 41(10): 4013-4021. |
| [58] | 王建营, 冯长根.螺噁嗪类光致变色化合物的合成研究进展[J].应用化学, 2007, 24(7): 729-736. |
| [58] | WANG Jianying, FENG Changgen.Progress on synthesis of photochromic spirooxazines[J].Chinese Journal of Applied Chemistry, 2007, 24(7): 729-736. |
| [59] | 余传明.含卟啉单元光致变色化合物的设计、合成与性能研究[D].南京:南京理工大学, 2017. |
| [59] | YU Chuanming.Design,synthesis and properties of photochromic compounds based on porphyrins[D].Nanjing:Nanjing University of Science and Technology, 2017. |
/
| 〈 |
|
〉 |