A General Synthetic Route to 3,5-Substituted Boron Dipyrromethenes: Applications and Properties

被引：41

作者：

Ulrich, Gilles ^{[1
]}

Ziessel, Raymond ^{[1
]}

Haefele, Alexandre ^{[1
]}

机构：

[1] CNRS UDS, UMR 7515, ECPM, LCOSA, F-67087 Strasbourg 02, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 09期

关键词：

SOLUBLE BODIPY DERIVATIVES; EFFICIENT ENERGY-TRANSFER; TUNABLE FLUORESCENT DYES; SENSITIZED SOLAR-CELLS; NEAR-INFRARED NIR; SPECTROSCOPIC PROPERTIES; STRUCTURAL CONTROL; ANION SENSORS; BORADIAZAINDACENE; COMPLEXES;

D O I：

10.1021/jo3002408

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient protocol for the direct synthesis of 3-substituted and 3,5-disubstituted BODIPY derivatives via electrophilic attack with NBS was developed. Various substituents like ethers, sugar, hydroxyl, thiophene, sulfur, azide, tertiary amines, alkyne, vinyl, or phosphonate groups were obtained in moderate to excellent yields. The amine-substituted derivatives display unusual spectroscopic and electrochemical properties which were analyzed in solution in the presence of HCl. The diethylamino-substituted derivative has a proton association constant of log beta = 4.7, and the disubstituted derivative has two association constants of log beta = 6.2 and 12.1 in ethanol. In both cases, the quenching of the fluorescence is explained by photoinduced electron transfer from the tertiary amine to the Bodipy excited state.

引用

页码：4298 / 4311

页数：14

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