Near-Infrared Photochromic Diarylethenes Based on the Changes in the π-Conjugated System and the Electronic Properties of the Heteroaryl Moieties

被引：6

作者：

Cheng, Hong-Bo ^{[1
]}

Tan, Xin ^{[1
]}

Pang, Mei-Li ^{[1
]}

机构：

[1] Nankai Univ, Dept Chem, Tianjin 300071, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 35期

基金：

中国国家自然科学基金;

关键词：

Photochromism; UV; Vis spectroscopy; Molecular electronics; Molecular devices; Diarylethenes; BEHAVIOR; DERIVATIVES; MODULATION; ABSORPTION; MEMORIES; UNIT;

D O I：

10.1002/ejoc.201301132

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

It is very challenging to construct photochromic materials with absorption and reactivity in the near-infrared (NIR) spectral region. Herein, four unsymmetrical diarylethene derivatives 1o-4o, which contain both indole and thiophene moieties, have been successfully synthesized, and their photochromic behaviors have been shifted to the NIR region. These newly developed NIR photochromic materials are highly sensitive and responsive to photostimuli both in solution and in poly(methyl methacrylate) films. It has been shown that 1o-4o exhibit remarkable UV/Vis and fluorescence spectral changes, allowing them to behave as reversible optical molecular switches in the NIR region.

引用

页码：7933 / 7940

页数：8

共 27 条

[1] Photochromism of dihydroindolizines Part VI: synthesis and photochromic behavior of a novel type of IR-absorbing photochromic compounds based on highly conjugated dihydroindolizines [J].

Ahmed, Saleh Abdel .

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2006, 19 (07) :402-414

[2] Light-Triggered Reversible Supramolecular Transformations of Multi-Bisthienylethene Hexagons [J].

Chen, Shangjun ;

Chen, Li-Jun ;

Yang, Hai-Bo ;

Tian, He ;

Zhu, Weihong .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) :13596-13599

[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] Dual-Stimulus Luminescent Lanthanide Molecular Switch Based on an Unsymmetrical Diarylperfluorocyclopentene [J].

Cheng, Hong-Bo ;

Zhang, Heng-Yi ;

Liu, Yu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (28) :10190-10193

[5] Bridging the Visible: The Modulation of the Absorption by More than 450 nm [J].

Delbaere, Stephanie ;

Vermeersch, Gaston ;

Frigoli, Michel ;

Mehl, Georg H. .

ORGANIC LETTERS, 2010, 12 (18) :4090-4093

[6] Single-Molecule Fluorescence Photoswitching of a Diarylethene-Perylenebisimide Dyad: Non-destructive Fluorescence Readout [J].

Fukaminato, Tuyoshi ;

Doi, Takao ;

Tamaoki, Nobuyuki ;

Okuno, Katsuki ;

Ishibashi, Yukihide ;

Miyasaka, Hiroshi ;

Irie, Masahiro .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (13) :4984-4990

[7] Diarylethenes for memories and switches [J].

Irie, M .

CHEMICAL REVIEWS, 2000, 100 (05) :1685-1716

[8] Near-infrared photochromic behavior in a donor-acceptor type diarylethene modulated by the cyanide anion [J].

Jin, Jiayu ;

Zhang, Junji ;

Zou, Lei ;

Tian, He .

ANALYST, 2013, 138 (06) :1641-1644

[9] Rapid and reversible shape changes of molecular crystals on photoirradiation [J].

Kobatake, Seiya ;

Takami, Shizuka ;

Muto, Hiroaki ;

Ishikawa, Tomoyuki ;

Irie, Masahiro .

NATURE, 2007, 446 (7137) :778-781

[10] Metal coordination-assisted near-infrared photochromic behavior: A large perturbation on absorption wavelength properties of N,N-donor ligands containing diarylethene derivatives by coordination to the rhenium(I) metal center [J].

Lee, Penny Ho-Man ;

Ko, Chi-Chiu ;

Zhu, Nianyong ;

Yam, Vivian Wing-Wah .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (19) :6058-+

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