Conformationally Restricted Dipyrromethene Boron Difluoride (BODIPY) Dyes: Highly Fluorescent, Multicolored Probes for Cellular Imaging

Abstract

Novel fluorescent, conformationally restricted dipyrromethene boron difluoride (BODIPY) dyes have been prepared by introducing a naphthalenyl group at the meso position of the BODIPY core. These BODIPY dyes exhibit increased fluorescence quantum yields compared with dyes that have a meso-position phenyl group with internal rotation. The absorption and emission wavelengths of such conformationally restricted BODIPY dyes can be easily tuned to the near-IR range by derivatization through a condensation reaction with benzaldehyde derivatives. The two-photon absorption properties of these BODIPY dyes were also investigated and the results show that they exhibit increased two-photon excited fluorescence compared to analogue dyes that contain a phenyl group. The one- and two-photon fluorescence imaging of living cells by using selected BODIPY dyes has been successfully demonstrated.

Strongly Emissive and Photostable Four‐Coordinate Organoboron N,C Chelates and Their Use in Fluorescence Microscopy

“…The magnitude of the obtained TPA cross sections, especially the one of dye 4, compares nicely with that of some of the best performing Bodipy derivatives that were used in TPE fluorescence imaging. [51][52][53] However, the plain Bodipy chromophore has commonly lower TPA cross sections (ca. 10 GM at 900 nm).…”

“…The results demonstrate the applicability of 4 as staining dye and the use of TPE is an additional surplus because of the deeper penetration of near-infrared excitation light into biological tissues. [51][52][53][54][55] …”

Optical signatures of borico dyes: a TD-DFT analysis

“…Indeed, BOD-IPY (boron-dipyrromethene), aza-BODIPY and boranil derivatives, that can all be viewed as constrained cyanines, have become key tools for biological, medicinal and analytical applications due to their excellent photophysical properties [1,2]. These molecules that are highly photostable and develop very large quantum yields, have found applications in several fields, e.g., ion sensing [3,4], nonlinear optics [5], photodynamic therapy [6], as well as fluorescence imaging [7]. Of course, more traditional series of fluorescent dyes have already found practical applications, and the two most well-known families of organic fluorophores remain coumarins and naphthalimides, that can be used as paper brighteners [8,9].…”

Novel Molecular Building Blocks Based on the Boradiazaindacene Chromophore: Applications in Fluorescent Metallosupramolecular Coordination Polymers

“…[20][21][22][23] In recent years, there has been a flurry of activity investigating many derivatives and numerous applications of these dyes. Among these, fluorescent chemosensors, [24][25][26][27] molecular logic gates, [28] fluorescent organogels, [29] sensitizers in dye-sensitized solar cells, [30,31] cellular imaging, [32] and applications in photodynamic therapy [33,34] are particularly noteworthy. There have also been previous reports of bipyridyl [35,36] and terpyridyl [37][38][39] derivatives of bodipy dyes and their Zn II complexes, although the monomeric derivatives were not designed for self-assembled polymerization.…”