Tailoring the properties of boron-dipyrromethene dyes with acetylenic functions at the 2,6,8 and 4-B substitution positions

被引：109

作者：

Bonardi, Laure ^{[1
]}

Ulrich, Gilles ^{[1
]}

Ziessel, Raymond ^{[1
]}

机构：

[1] Univ Strasbourg 1, CNRS, LCOSA, ECPM, F-67087 Strasbourg 02, France

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 11期

关键词：

D O I：

10.1021/ol800560b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Substitution of F-Bodipy with alkynylaryl residues at boron, at the pyrrolic core or at the meso position, provides unique tri-, tetra-, and pentasubstituted dyes. Substitution at the (pyrrolic) 2,6-positions provides substantial red shifts with quantum yields in the 40-90% range and excited-state lifetimes of 3-7 ns. ON/OFF fluorescence switching can be produced by protonation of dibutylamino subunits.

引用

页码：2183 / 2186

页数：4

共 16 条

[1] PYRROMETHENE-BF2 COMPLEXES AS LASER-DYES .2. [J].

BOYER, JH ;

HAAG, AM ;

SATHYAMOORTHI, G ;

SOONG, ML ;

THANGARAJ, K ;

PAVLOPOULOS, TG .

HETEROATOM CHEMISTRY, 1993, 4 (01) :39-49

[2] 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes modified for extended conjugation and restricted bond rotations [J].

Chen, J ;

Burghart, A ;

Derecskei-Kovacs, A ;

Burgess, K .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10) :2900-2906

[3]

EUGENE OR, 1996, HDB FLUORESCENT PROB

[4] In vitro demonstration of the heavy-atom effect for photodynamic therapy [J].

Gorman, A ;

Killoran, J ;

O'Shea, C ;

Kenna, T ;

Gallagher, WM ;

O'Shea, DF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (34) :10619-10631

[5] Tetrahedral boron chemistry for the preparation of highly efficient "Cascatelle" devices [J].

Goze, Christine ;

Ulrich, Gilles ;

Ziessel, Raymond .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (02) :313-322

[6] BODIPY dyes and their derivatives: Syntheses and spectroscopic properties [J].

Loudet, Aurore ;

Burgess, Kevin .

CHEMICAL REVIEWS, 2007, 107 (11) :4891-4932

[7] A selective and sensitive fluoroionophore for HgII, AgI, and CuII with virtually decoupled fluorophore and receptor units [J].

Rurack, K ;

Kollmannsberger, M ;

Resch-Genger, U ;

Daub, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (05) :968-969

[8] Excimer emission and energy transfer in cofacial boradiazaindacene (BODIPY) dimers built on a xanthene scaffold [J].

Saki, N ;

Dinc, T ;

Akkaya, EU .

TETRAHEDRON, 2006, 62 (11) :2721-2725

[9] LASER ACTIVE CYANOPYRROMETHENE-BF2 COMPLEXES [J].

SATHYAMOORTHI, G ;

BOYER, JH ;

ALLIK, TH ;

CHANDRA, S .

HETEROATOM CHEMISTRY, 1994, 5 (04) :403-407

[10] Spectral dispersion and water solubilization of BODIPY dyes via palladium-catalyzed C-H functionalization [J].

Thivierge, Cliferson ;

Bandichhor, Rakeshwar ;

Burgess, Kevin .

ORGANIC LETTERS, 2007, 9 (11) :2135-2138

← 1 2 →