Near-infrared fluorophores containing benzo[c]heterocycle subunits

被引:70
作者
Meek, Scott T. [1 ]
Nesterov, Evgueni E. [1 ]
Swager, Timothy M. [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
D O I
10.1021/ol800988w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The syntheses and spectroscopic properties of eight new push-pull-type near-infrared fluorophores that contain either isobenzofuran or isothianaphthene subunits are presented. The isobenzofuran dyes demonstrate significantly red-shifted absorption compared with their isothianaphthene counterparts, which is attributed to isobenzofuran's more potent pro-quinoidal character.
引用
收藏
页码:2991 / 2993
页数:3
相关论文
共 22 条
[1]   CONDENSATION OF PHTHALALDEHYDIC ACID WITH MONOSUBSTITUTED BENZENES [J].
ALHAMDANY, R ;
ALRAWI, JM ;
IBRAHIM, S .
JOURNAL FUR PRAKTISCHE CHEMIE, 1987, 329 (01) :126-130
[2]   INDANE-1,3-DIONE, PHTHALIMIDINE AND PHTHALIDE DERIVATIVES AS ALKYLATING-AGENTS [J].
BARILI, PL ;
SCARTONI, V .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1985, 22 (05) :1199-1202
[3]   In vivo imaging of proteolytic activity in atherosclerosis [J].
Chen, JQ ;
Tung, CH ;
Mahmood, U ;
Ntziachristos, V ;
Gyurko, R ;
Fishman, MC ;
Huang, PL ;
Weissleder, R .
CIRCULATION, 2002, 105 (23) :2766-2771
[4]   In vivo near-infrared fluorescence imaging [J].
Frangioni, JV .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2003, 7 (05) :626-634
[5]   LEWIS-ACID-CATALYZED REACTION OF OXYGEN WITH 1,3-DIPHENYLISOBENZOFURAN, TETRAPHENYLFURAN AND TETRAPHENYLCYCLOPENTADIENE [J].
HAYNES, RK ;
PETERS, JM ;
WILMOT, ID .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1980, 33 (12) :2653-2661
[6]   In vivo detection of amyloid-β deposits by near-infrared imaging using an oxazine-derivative probe [J].
Hintersteiner, M ;
Enz, A ;
Frey, P ;
Jaton, AL ;
Kinzy, W ;
Kneuer, R ;
Neumann, U ;
Rudin, M ;
Staufenbiel, M ;
Stoeckli, M ;
Wiederhold, KH ;
Gremlich, HU .
NATURE BIOTECHNOLOGY, 2005, 23 (05) :577-583
[7]   LOW-BANDGAP CONJUGATED POLYMERS - A JOINT EXPERIMENTAL AND THEORETICAL-STUDY OF THE STRUCTURE OF POLYISOTHIANAPHTHENE [J].
HOOGMARTENS, I ;
ADRIAENSENS, P ;
VANDERZANDE, D ;
GELAN, J ;
QUATTROCCHI, C ;
LAZZARONI, R ;
BREDAS, JL .
MACROMOLECULES, 1992, 25 (26) :7347-7356
[8]   SYNTHESIS OF 3 ISOMERIC ORTHO-SUBSTITUTED PHENYLTHIENYL BENZOIC-ACIDS [J].
JOHNSON, AL .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (08) :1320-1324
[9]   The estimation of the aromaticity of five-membered and benzo fused five-membered rings by the hybrid DFT computed magnetic properties [J].
Jursic, BS .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1996, 33 (04) :1079-1081
[10]   Enhancement of green electroluminescence from 2,5-di-p-anisyl-isobenzofuran by double-layer doping strategy [J].
Li, JY ;
Hong, ZR ;
Wang, PF ;
Lee, CS ;
Wong, NB ;
Kwong, HL ;
Lee, ST .
THIN SOLID FILMS, 2004, 446 (01) :111-116