Preparation of Viscosity-Sensitive Isoxazoline/Isoxazolyl-Based Molecular Rotors and Directly Linked BODIPY-Fulleroisoxazoline from the Stable meso-(Nitrile Oxide)-Substituted BODIPY

被引：38

作者：

Zatsikha, Yuriy V. ^{[1
]}

Didukh, Natalia O. ^{[1
,2
]}

Swedin, Rachel K. ^{[3
]}

Yakubovskyi, Viktor P. ^{[2
]}

Blesener, Tanner S. ^{[1
]}

Healy, Andrew T. ^{[3
]}

Herbert, David E. ^{[1
]}

Blank, David A. ^{[3
]}

Nemykin, Victor N. ^{[1
]}

Kovtun, Yuriy P. ^{[2
]}

机构：

[1] Univ Manitoba, Dept Chem, Winnipeg, MB R3T 2N2, Canada

[2] Natl Acad Sci Ukraine, Inst Organ Chem, 5 Murmanska Str, UA-02660 Kiev, Ukraine

[3] Univ Minnesota, Dept Chem, 207 Pleasant St SE, Minneapolis, MN 55455 USA

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 14期

基金：

加拿大自然科学与工程研究理事会;

关键词：

NITRILE N-OXIDES; PHOTOPHYSICAL PROPERTIES; CYCLOADDITION; DYES; DERIVATIVES; ISOXAZOLES; CHEMISTRY; DIPYRROMETHENES; REDOX;

D O I：

10.1021/acs.orglett.9b02082

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We developed a simple methodology for the preparation of stable meso-(nitrile oxide)-substituted BODIPYs, which were characterized by spectroscopic methods and X-ray crystallography. These compounds were used for the preparation of isoxazoline- or isoxazolyl-BODIPYs by 1,3-dipolar cycloaddition reaction with dipolarophiles. Several BODIPYs possess molecular rotor behavior, including viscosity-dependent fluorescence. Transient absorption spectroscopy and time-resolved fluorescence are indicative of a 3 orders of magnitude difference in the excited-state lifetime for dichloromethane and glycerol solutions.

引用

页码：5713 / 5718

页数：6