In situ preparation of highly fluorescent pyrene-dyes from non-luminous precursors upon photoirradiation

被引:16
作者
Aotake, Tatsuya [1 ]
Tanimoto, Hiroshi [2 ]
Hotta, Hidekatsu [2 ]
Kuzuhara, Daiki [1 ]
Okujima, Tetsuo [2 ]
Uno, Hidemitsu [2 ]
Yamada, Hiroko [1 ,3 ]
机构
[1] Nara Inst Sci & Technol, Grad Sch Mat Sci, Ikoma 6300192, Japan
[2] Ehime Univ, Dept Biol & Chem, Grad Sch Sci & Engn, Matsuyama, Ehime 7908577, Japan
[3] JST, CREST, Chiyoda Ku, Tokyo 1020076, Japan
关键词
PHOTOCHEMICAL-SYNTHESIS; CHEMISTRY;
D O I
10.1039/c3cc40827b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The non-luminous precursor, 2-(1-pyrenyl)-9,10-dihydro-9,10-ethanoanthracene-11,12-dione, was photochemically converted to highly-fluorescent 2-(1-pyrenyl) anthracene quantitatively in solution and in the PMMA film and the fluorescence quantum yield of the acene in benzonitrile was as high as 0.99.
引用
收藏
页码:3661 / 3663
页数:3
相关论文
共 26 条
[1]   Photochemical synthesis of naphthacene and its derivatives for irreversible photo-responsive fluorescent molecules [J].
Aotake, Tatsuya ;
Yamashita, Yuko ;
Okujima, Tetsuo ;
Shirasawa, Nobuhiko ;
Jo, Yukari ;
Fujimori, Shigeo ;
Uno, Hidemitsu ;
Ono, Noboru ;
Yamada, Hiroko .
TETRAHEDRON LETTERS, 2013, 54 (14) :1790-1793
[2]   Synthesis, Structure, and Photochemistry of 5,14-Diketopentacene [J].
Aotake, Tatsuya ;
Ikeda, Shinya ;
Kuzuhara, Daiki ;
Mori, Shigeki ;
Okujima, Tetsuo ;
Uno, Hidemitsu ;
Yamada, Hiroko .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (09) :1723-1729
[3]   Electronic decoupling in ground and excited states of asymmetric biaryls [J].
Baumgarten, M ;
Gherghel, L ;
Friedrich, J ;
Jurczok, M ;
Rettig, W .
JOURNAL OF PHYSICAL CHEMISTRY A, 2000, 104 (06) :1130-1140
[4]   Rhodamines NN: A Novel Class of Caged Fluorescent Dyes [J].
Belov, Vladimir N. ;
Wurm, Christian A. ;
Boyarskiy, Vadim P. ;
Jakobs, Stefan ;
Hell, Stefan W. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (20) :3520-3523
[5]   Imaging intracellular fluorescent proteins at nanometer resolution [J].
Betzig, Eric ;
Patterson, George H. ;
Sougrat, Rachid ;
Lindwasser, O. Wolf ;
Olenych, Scott ;
Bonifacino, Juan S. ;
Davidson, Michael W. ;
Lippincott-Schwartz, Jennifer ;
Hess, Harald F. .
SCIENCE, 2006, 313 (5793) :1642-1645
[6]   Subdiffraction imaging through the selective donut-mode depletion of thermally stable photoswitchable fluorophores: Numerical analysis and application to the fluorescent protein Dronpa [J].
Dedecker, Peter ;
Hotta, Jun-Ichi ;
Flors, Cristina ;
Sliwa, Michel ;
Uji-, Hiroshi, I ;
Roeffaers, Maarten B. J. ;
Ando, Ryoko ;
Mizuno, Hideaki ;
Miyawaki, Atsushi ;
Hofkens, Johan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (51) :16132-16141
[7]   Far-field optical nanoscopy [J].
Hell, Stefan W. .
SCIENCE, 2007, 316 (5828) :1153-1158
[8]   Ultra-high resolution imaging by fluorescence photoactivation localization microscopy [J].
Hess, Samuel T. ;
Girirajan, Thanu P. K. ;
Mason, Michael D. .
BIOPHYSICAL JOURNAL, 2006, 91 (11) :4258-4272
[9]   Organic chemistry: A digital fluorescent molecular photoswitch [J].
Irie, M ;
Fukaminato, T ;
Sasaki, T ;
Tamai, N ;
Kawai, T .
NATURE, 2002, 420 (6917) :759-760
[10]   Photochemical synthesis of tetraaryl-substituted pentacenes [J].
Katsuta, Shuhei ;
Yamada, Hiroko ;
Okujima, Tetsuo ;
Uno, Hidemitsu .
TETRAHEDRON LETTERS, 2010, 51 (10) :1397-1400