Novel photochromic molecules based on 4,5-dithienyl thiazole with fast thermal bleaching rate

被引:138
作者
Kawai, Shigekazu [1 ]
Nakashima, Takuya [1 ]
Atsumi, Kazuhiko [1 ]
Sakai, Toshiyuki [1 ]
Harigai, Miki [1 ]
Imamoto, Yasushi [1 ]
Kamikubo, Hironari [1 ]
Kataoka, Mikio [1 ]
Kawai, Tsuyoshi [1 ]
机构
[1] Nara Inst Sci & Technol, NAIST, Grad Sch Mat Sci, Nara 6300192, Japan
关键词
D O I
10.1021/cm0630340
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Novel photochromic triangle terarylenes are synthesized, and their photochromic properties and thermal bleaching kinetics are investigated. Fairly high photochemical coloration reactivity is observed with photochemical quantum yield as high as 0.6 for 4,5-dithienyl thiazole derivative. Introduction of phenyl-ethynyl groups into the molecular structure allows systematic control of thermal cycloreversion time constant over 10(5) times, and the half-lifetime shorter than 2 s is achieved at 303 K. The kinetic analysis of thermal cycloreversion reaction clearly shows significant contribution of frequency factor A. A novel molecular designing concept for systematic control of thermal bleaching reaction rate is presented without taking bulky functional groups on reaction center.
引用
收藏
页码:3479 / 3483
页数:5
相关论文
共 54 条
[1]   Large and stable refractive index change in photochromic hybrid materials [J].
Biteau, J ;
Chaput, F ;
Lahlil, K ;
Boilot, JP ;
Tsivgoulis, GM ;
Lehn, JM ;
Darracq, B ;
Marois, C ;
Levy, Y .
CHEMISTRY OF MATERIALS, 1998, 10 (07) :1945-1950
[2]  
Brown G. H., 1971, Photochromism
[3]   Photochemical and thermal behaviour of new photochromic indeno-fused naphthopyrans [J].
Coelho, PJ ;
Salvador, MA ;
Oliveira, MM ;
Carvalho, LM .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2005, 172 (03) :300-307
[4]  
Crano JC, 1999, T APPL CHEM, P1
[5]   One-way optoelectronic switching of photochromic molecules on gold [J].
Dulic, D ;
van der Molen, SJ ;
Kudernac, T ;
Jonkman, HT ;
de Jong, JJD ;
Bowden, TN ;
van Esch, J ;
Feringa, BL ;
van Wees, BJ .
PHYSICAL REVIEW LETTERS, 2003, 91 (20)
[6]   SELF-HOLDING PHOTOCHROMIC POLYMER MACH-ZEHNDER OPTICAL SWITCH [J].
EBISAWA, F ;
HOSHINO, M ;
SUKEGAWA, K .
APPLIED PHYSICS LETTERS, 1994, 65 (23) :2919-2921
[7]   THERMALLY REVERSIBLE PHOTOCONVERSION OF SPIROINDOLINE-NAPHTHO-OXAZINES TO PHOTOMEROCYANINES - A PHOTOCHEMICAL AND KINETIC-STUDY [J].
FAVARO, G ;
MALATESTA, V ;
MAZZUCATO, U ;
OTTAVI, G ;
ROMANI, A .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1995, 87 (03) :235-241
[8]   Three-dimensional erasable optical memory using a photochromic diarylethene single crystal as the recording medium [J].
Fukaminato, T ;
Kobatake, S ;
Kawai, T ;
Irie, M .
PROCEEDINGS OF THE JAPAN ACADEMY SERIES B-PHYSICAL AND BIOLOGICAL SCIENCES, 2001, 77 (02) :30-35
[9]   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
[10]   PHOTOCHROMIC HETEROCYCLIC FULGIDES .1. REARRANGEMENT REACTIONS OF (E)-ALPHA-3-FURYLETHYLIDENE(ISOPROPYLIDENE)SUCCINIC ANHYDRIDE [J].
HELLER, HG ;
OLIVER, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (01) :197-202