Molecular design of novel non-planar heteropolycyclic fluorophores with bulky substituents: convenient synthesis and solid-state fluorescence characterization

被引:66
作者
Ooyama, Yousuke [1 ]
Yoshikawa, Shintaro [1 ]
Watanabe, Shigeru [1 ]
Yoshida, Katsuhira [1 ]
机构
[1] Kochi Univ, Fac Sci, Dept Mat Sci, Kochi 7808520, Japan
关键词
D O I
10.1039/b607891e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Novel indeno[1,2-b] benzo[4,5-e] pyran-11-one-type fluorophores exhibiting intense solid-state fluorescence were conveniently synthesized and the relation between their solid-state photophysical properties and the X-ray crystal structures were investigated, which demonstrates that non-planar structures with sterical hindered substituents prevent the fluorophores from forming short pi - pi contacts causing fluorescence quenching in the solid state.
引用
收藏
页码:3406 / 3409
页数:4
相关论文
共 37 条
[1]   Evolution of red organic light-emitting diodes: Materials and devices [J].
Chen, CT .
CHEMISTRY OF MATERIALS, 2004, 16 (23) :4389-4400
[2]   Red-emitting fluorenes as efficient emitting hosts for non-doped, organic red-light-emitting diodes [J].
Chiang, CL ;
Wu, MT ;
Dai, DC ;
Wen, YS ;
Wang, JK ;
Chen, CT .
ADVANCED FUNCTIONAL MATERIALS, 2005, 15 (02) :231-238
[3]   Observation of a non-conventional Horner-Wadsworth-Emmons olefination product and the effect of the lateral ethyl substitution on the solid state fluorescence [J].
Davis, R ;
Abraham, S ;
Rath, NP ;
Das, S .
NEW JOURNAL OF CHEMISTRY, 2004, 28 (11) :1368-1372
[4]   Molecular mechanism of the solid-state fluorescence behavior of the organic pigment yellow 101 and its derivatives [J].
Dreuw, A ;
Plötner, A ;
Lorenz, L ;
Wachtveitl, J ;
Djanhan, JE ;
Brüning, B ;
Metz, T ;
Bolte, M ;
Schmidt, MU .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (47) :7783-7786
[5]  
DREUW A, 2005, ANGEW CHEM, V117, P7961
[6]  
Fei Z, 2003, ANGEW CHEM, V115, P807
[7]   Single crystals of the disubstituted anthracene 9,10-(Ph2P=S)2C14H8 selectively and reversibly detect toluene by solid-state fluorescence emission [J].
Fei, ZF ;
Kocher, N ;
Mohrschladt, CJ ;
Ihmels, H ;
Stalke, D .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (07) :783-787
[8]   Unusual fluorescent properties of novel fluorophores, 6-aryl-3,4-diphenyl-α-pyrone derivatives [J].
Hirano, K ;
Minakata, S ;
Komatsu, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2001, 74 (09) :1567-1575
[9]   Optical properties of novel 2,3-dicyano-5-methyl-6H-1,4-diazepine dyes in the solid state [J].
Horiguchi, E ;
Matsumoto, S ;
Funabiki, K ;
Matsui, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2005, 78 (06) :1167-1173
[10]  
Kraft A, 1998, ANGEW CHEM INT EDIT, V37, P402, DOI 10.1002/(SICI)1521-3773(19980302)37:4<402::AID-ANIE402>3.0.CO