Photochromism of a novel asymmetrical diarylethene with a (formyloxyethoxy)ethyl-linked naphthalimide moiety

被引:6
作者
Li, Xue [1 ]
Liu, Gang [1 ]
Pu, Shouzhi [1 ]
机构
[1] Jiangxi Sci & Technol Normal Univ, Jiangxi Key Lab Organ Chem, Nanchang 330013, Peoples R China
基金
中国国家自然科学基金;
关键词
diarylethene; fluorescence switch; naphthalimide; photoirradiaton; photochromism; NONDESTRUCTIVE READOUT; LOGIC GATES; DERIVATIVES; UNIT; FLUORESCENCE; SWITCHES; BISTHIENYLETHENE; MODULATION; REACTIVITY; PROPERTY;
D O I
10.1002/poc.3336
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel asymmetrical diarylethene with a (formyloxyethoxy)ethyl-linked naphthalimide unit was synthesized, and its photochromic and fluorescence properties were systematically investigated in both solution and a poly(metyl methacrylate) film. The diarylethene showed significant photochromism and notable fluorescence switching properties upon irradiation with ultraviolet/visible light. Compared with the parent diarylethene, introduction of the naphthalimide moiety was effective to increase the molar absorption coefficient, the fluorescence quantum yield, and fluorescent modulation efficiency of the diarylethene. Copyright (C) 2014 John Wiley & Sons, Ltd.
引用
收藏
页码:764 / 769
页数:6
相关论文
共 52 条
[1]   Reversible photoinduced change in molecular ordering of diarylethene derivatives at a solution-HOPG interface [J].
Arai, Ryota ;
Uemura, Shinobu ;
Irie, Masahiro ;
Matsuda, Kenji .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) :9371-9379
[2]   Fluorescence and Morphology Modulation in a Photochromic Diarylethene Self-Assembly System [J].
Cao, Xinhua ;
Zhou, Jing ;
Zou, Ying ;
Zhang, Mingming ;
Yu, Xudong ;
Zhang, Song ;
Yi, Tao ;
Huang, Chunhui .
LANGMUIR, 2011, 27 (08) :5090-5097
[3]   Multi-addressable photochromic terarylene containing benzo[b]thiophene-1,1-dioxide unit as ethene bridge: multifunctional molecular logic gates on unimolecular platform [J].
Chen, Shangjun ;
Yang, Yuheng ;
Wu, Yue ;
Tian, He ;
Zhu, Weihong .
JOURNAL OF MATERIALS CHEMISTRY, 2012, 22 (12) :5486-5494
[4]   A New Prodrug-Derived Ratiometric Fluorescent Probe for Hypoxia: High Selectivity of Nitroreductase and Imaging in Tumor Cell [J].
Cui, Lei ;
Zhong, Ye ;
Zhu, Weiping ;
Xu, Yufang ;
Du, Qingshan ;
Wang, Xin ;
Qian, Xuhong ;
Xiao, Yi .
ORGANIC LETTERS, 2011, 13 (05) :928-931
[5]   Comprehensive model of the photophysics of N-phenylnaphthalimides: The role of solvent and rotational relaxation [J].
Demeter, A ;
Berces, T ;
Biczok, L ;
Wintgens, V ;
Valat, P ;
Kossanyi, J .
JOURNAL OF PHYSICAL CHEMISTRY, 1996, 100 (06) :2001-2011
[6]   A contribution to the design of molecular switches: Novel acid-mediated ring-closing-photochemical ring-opening of 2,3-bis(heteroaryl)quinones (heteroaryl = thienyl, furanyl, pyrrolyl) [J].
Deng, XH ;
Liebeskind, LS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (31) :7703-7704
[7]   Colorimetric and fluorescent anion sensors: an overview of recent developments in the use of 1,8-naphthalimide-based chemosensors [J].
Duke, Rebecca M. ;
Veale, Emma B. ;
Pfeffer, Frederick M. ;
Kruger, Paul E. ;
Gunnlaugsson, Thorfinnur .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (10) :3936-3953
[8]   Digital photoswitching of fluorescence based on the photochromism of diarylethene derivatives at a single-molecule level [J].
Fukaminato, T ;
Sasaki, T ;
Kawai, T ;
Tamai, N ;
Irie, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (45) :14843-14849
[9]   Photochromism of diarylethene single molecules in polymer matrices [J].
Fukaminato, Tuyoshi ;
Umemoto, Tohru ;
Iwata, Yasuhide ;
Yokojima, Satoshi ;
Yoneyama, Mitsuru ;
Nakamura, Shinichiro ;
Irie, Masahiro .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (18) :5932-5938
[10]   Diheteroarylethenes as thermally stable photoswitchable acceptors in photochromic fluorescence resonance energy transfer (pcFRET) [J].
Giordano, L ;
Jovin, TM ;
Irie, M ;
Jares-Erijman, EA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (25) :7481-7489