Synthesis and properties of photochromic spirooxazine with aggregation-induced emission fluorophores polymeric nanoparticles

被引:42
作者
Li, Xue [1 ,2 ]
Li, Chengpeng [2 ]
Wang, Sheng [1 ,2 ]
Dong, Huan [3 ,4 ]
Ma, Xiang [3 ,4 ]
Cao, Derong [1 ]
机构
[1] South China Univ Technol, Sch Chem & Chem Engn, State Key Lab Luminescent Mat & Devices, Guangzhou 510641, Guangdong, Peoples R China
[2] Lingnan Normal Univ, Dev Ctr New Mat Engn & Technol Univ Guangdong, Sch Chem & Chem Engn, Zhanjiang 524048, Peoples R China
[3] East China Univ Sci & Technol, Key Lab Adv Mat, Meilong Rd 130, Shanghai 200237, Peoples R China
[4] East China Univ Sci & Technol, Inst Fine Chem, Meilong Rd 130, Shanghai 200237, Peoples R China
关键词
Spirooxazine dye; Photochromism; Polymeric nanoparticles; Aggregation-induced emission; Tetraphenylethylene derivative; CARBAZOLE-SPIRONAPHTHOXAZINE COPOLYMER; POLY(N-ISOPROPYLACRYLAMIDE) HYDROGEL; SWITCHING PROPERTIES; FLUORESCENT-PROBE; DERIVATIVES; DYE; ENHANCEMENT; MOLECULES; MEMORIES; CRYSTALS;
D O I
10.1016/j.dyepig.2017.03.068
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
We designed and synthesized photochromic fluorescent poly (MMA-co-SPO-co-TPE) nanoparticles with pendant spirooxazine (SPO) dye and tetraphenylethylene (TPE) fuorophores attached to poly (methyl methacrylate) (MMA) backbone by semi-continuous polymerization. The polymerization reactions were accomplished in water with randomly methylated-fi-cyclodextrin (beta-CD) at 80 degrees C in the presence of potassium peroxodisulfate which can be.used as free radical initiator. This new synthetic method leads to uniform and smooth nanoparticles with a narrow particle size distribution. In addition, the poly (MMA-co-SPO-co-TPE) nanoparticles exhibit aggregation induced emission (ME) properties and excellent photochemical properties because of spirooxazine dyes convert reversibly to merocyanine form upon ultraviolet (UV) irradiation, which active the intramolecular energy transfer pathway and quench the fluorescence of TPE in polymers. Consequently, the fluorescence of the poly (MMA-co-SPO-co-TPE) nanoparticles can be reversibly switched "on" and "off' upon UV and visible light, which maybe have potential application in biological fluorescent labeling as well as in optical fields like individually light-addressable nanoscale devices. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:481 / 490
页数:10
相关论文
共 48 条
[21]   Highly Fluorescent Chameleon Nanoparticles and Polymer Films: Multicomponent Organic Systems that Combine FRET and Photochromic Switching [J].
Kim, Sanghoon ;
Yoon, Seong-Jun ;
Park, Soo Young .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (29) :12091-12097
[22]   Surface plasmon resonance spectroscopy on the interaction of a self-assembled monolayer with linear hydrocarbon such as pentane, hexane, heptane and octane [J].
Kim, SH ;
Choi, SW ;
Suh, HJ ;
Jin, SH ;
Gal, YS ;
Koh, K .
DYES AND PIGMENTS, 2002, 55 (01) :17-25
[23]   Photoregulated optical switching of poly(N-isopropylacrylamide) hydrogel in aqueous solution with covalently attached spironaphthoxazine and D-π-A type pyran-based fluorescent dye [J].
Kim, Sung-Hoon ;
Hwang, In-Jeong ;
Gwon, Seon-Yeong ;
Son, Young-A .
DYES AND PIGMENTS, 2010, 87 (02) :158-163
[24]   Multiple switching behaviors of poly(N-isopropylacrylamide) hydrogel with spironaphthoxazine and D-π-A type dye [J].
Lee, Eun-Mi ;
Gwon, Seon-Yeong ;
Ji, Byung-Chul ;
Wang, Sheng ;
Kim, Sung-Hoon .
JOURNAL OF LUMINESCENCE, 2012, 132 (03) :665-670
[25]   Switching properties of fluorescent photochromic poly(methyl methacrylate) with spironaphthoxazine and D-π-A type pyran-based fluorescent dye [J].
Lee, Eun-Mi ;
Gwon, Seon-Young ;
Son, Young-A ;
Kim, Sung-Hoon .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2012, 86 :600-604
[26]   New thermally stable aggregation-induced emission enhancement compounds for non-doped red organic light-emitting diodes [J].
Li, Haiyin ;
Chi, Zhenguo ;
Zhang, Xiqi ;
Xu, Bingjia ;
Liu, Siwei ;
Zhang, Yi ;
Xu, Jiarui .
CHEMICAL COMMUNICATIONS, 2011, 47 (40) :11273-11275
[27]   Synthesis and properties of a new class of aggregation-induced enhanced emission compounds: Intense blue light emitting triphenylethylene derivatives [J].
Liu, Cong ;
He, Wen ;
Shi, Guang ;
Luo, Haiyuan ;
Zhang, Song ;
Chi, Zhenguo .
DYES AND PIGMENTS, 2015, 112 :154-161
[28]   Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole [J].
Luo, JD ;
Xie, ZL ;
Lam, JWY ;
Cheng, L ;
Chen, HY ;
Qiu, CF ;
Kwok, HS ;
Zhan, XW ;
Liu, YQ ;
Zhu, DB ;
Tang, BZ .
CHEMICAL COMMUNICATIONS, 2001, (18) :1740-1741
[29]   Novel organogel harnessing Excited-State Intramolecular Proton Transfer process with aggregation induced emission and photochromism [J].
Luo, Miao ;
Wang, Sheng ;
Wang, Meiling ;
Huang, Shaorong ;
Li, Chengpeng ;
Chen, Lin ;
Ma, Xiang .
DYES AND PIGMENTS, 2016, 132 :48-57
[30]   PHOTOCHROMIC SPIRONAPHTHOXAZINES - A THEORETICAL-STUDY [J].
MALATESTA, V ;
RANGHINO, G ;
ROMANO, U ;
ALLEGRINI, P .
INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, 1992, 42 (04) :879-887