Synthesis and Spectroscopic and Cellular Properties of Near-IR [a]Phenanthrene-Fused 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacenes

被引：32

作者：

Zhao, Ning ^{[1
]}

Xuan, Sunting ^{[1
]}

Zhou, Zehua ^{[1
]}

Fronczek, Frank R. ^{[1
]}

Smith, Kevin M. ^{[1
]}

Vicente, M. Graca H. ^{[1
]}

机构：

[1] Louisiana State Univ, Dept Chem, Baton Rouge, LA 70803 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 18期

关键词：

BODIPY DYES SYNTHESIS; BORON-DIPYRROMETHENES; REGIOSELECTIVE FUNCTIONALIZATION; FUSED BODIPY; RED; AZADIPYRROMETHENES; ABSORPTION; CHEMISTRY; BRIGHT; SERIES;

D O I：

10.1021/acs.joc.7b01940

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new synthetic method to build aryl-fused 4,4-difluoro-4-bora-3a,4a-diaza-s-indacenes (BODIPYs) is reported. The intramolecular cyclization step was completed in a short time (1-2 h) and in high yields (>90%), due to the intrinsic rigid structural conformation of the precursor BODIPY and the high reactivity of its 1,7-bromo groups. The [a]phenanthrene-fused BODIPYs 4a c were characterized by NMR spectroscopy, HRMS, DFT calculations, and, in the case of 4a, by X-ray crystallography. Spectroscopic studies show that 4a-c strongly absorb and emit in the NIR spectral region, in the range 642-701 nm. In addition, BODIPYs 4b and 4c exhibit no toxicity in the light or dark in HEp2 cells and accumulate intracellularly in a time-dependent manner, mainly in the cell endoplasmic reticulum. These results suggest the potential use of [a] phenanthrene-fused BODIPYs as NIR bioimaging probes.

引用

页码：9744 / 9750

页数：7