Improved synthesis of 2,2'-dibromo-9,9'-spirobifluorene and its 2,2'-bisdonor-7,7'-bisacceptor-substituted fluorescent derivatives

被引:68
作者
Chiang, CL [1 ]
Shu, CF
Chen, CT
机构
[1] Acad Sinica, Inst Chem, Taipei 11529, Taiwan
[2] Natl Chiao Tung Univ, Dept Appl Chem, Hsinchu 30035, Taiwan
[3] Acad Sinica, Inst Chem, Taipei 11529, Taiwan
关键词
D O I
10.1021/ol0513591
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[graphics] Pure 2,2'-Dibromo-9,9'-spirobifluorene was synthesized by a method that did not involve troublesome dibromination of 9,9'-spirobifluorene or Sandmeyer reaction of 2,2'-diamino-9,9'-spirobifluorene. A series of donor-acceptor orthogonally substituted 9,9'-spirobifluorene was subsequently prepared showing rich variation of fluorescence in solution and in solid state.
引用
收藏
页码:3717 / 3720
页数:4
相关论文
共 33 条
[1]   π-conjugated twin molecules based on truxene:: Synthesis and optical properties [J].
Cao, XY ;
Zhang, W ;
Zi, H ;
Pei, J .
ORGANIC LETTERS, 2004, 6 (26) :4845-4848
[2]   Synthesis and optical resolution of 9,9'-spirobifluorene-1, 1'-diol [J].
Cheng, X ;
Hou, GH ;
Xie, JH ;
Zhou, QL .
ORGANIC LETTERS, 2004, 6 (14) :2381-2383
[3]   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
[4]   Syntheses and spectroscopic studies of spirobifluorene-bridged bipolar systems; photoinduced electron transfer reactions [J].
Chien, YY ;
Wong, KT ;
Chou, PT ;
Cheng, YM .
CHEMICAL COMMUNICATIONS, 2002, (23) :2874-2875
[5]   White organic light-emitting diodes based on 2,7-bis(2,2-diphenylvinyl)-9,9′-spirobifluorene:: Improvement in operational lifetime [J].
Chuen, CH ;
Tao, YT ;
Wu, FI ;
Shu, CF .
APPLIED PHYSICS LETTERS, 2004, 85 (20) :4609-4611
[6]   Spiran with four aromatic radicals on the spiro carbon atom [J].
Clarkson, RG ;
Gomberg, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1930, 52 :2881-2891
[7]   An improved experimental determination of external photoluminescence quantum efficiency [J].
deMello, JC ;
Wittmann, HF ;
Friend, RH .
ADVANCED MATERIALS, 1997, 9 (03) :230-&
[8]   ALKYL NITRITE-METAL HALIDE DEAMINATION REACTIONS .7. SYNTHETIC COUPLING OF ELECTROPHILIC BROMINATION WITH SUBSTITUTIVE DEAMINATION FOR SELECTIVE SYNTHESIS OF MULTIPLY BROMINATED AROMATIC-COMPOUNDS FROM ARYLAMINES [J].
DOYLE, MP ;
VANLENTE, MA ;
MOWAT, R ;
FOBARE, WF .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (13) :2570-2575
[9]   ALKYL NITRITE METAL HALIDE DEAMINATION REACTIONS .2. SUBSTITUTIVE DEAMINATION OF ARYLAMINES BY ALKYL NITRITES AND COPPER(II) HALIDES - DIRECT AND REMARKABLY EFFICIENT CONVERSION OF ARYLAMINES TO ARYL HALIDES [J].
DOYLE, MP ;
SIEGFRIED, B ;
DELLARIA, JF .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (14) :2426-2431
[10]   Electrogenerated chemiluminescence. 81. Influence of donor and acceptor substituents on the ECL of a spirobifluorene-bridged bipolar system [J].
Fungo, F ;
Wong, KT ;
Ku, SY ;
Hung, YY ;
Bard, AJ .
JOURNAL OF PHYSICAL CHEMISTRY B, 2005, 109 (09) :3984-3989