Optimization of Aqueous Stability versus π‐Conjugation in Tetracationic Bis(triarylborane) Chromophores: Applications in Live‐Cell Fluorescence Imaging

Abstract

The stability of tetracationic triarylboranes in dilute aqueous solution wasi nvestigated by tuning the steric demando ft he linker in a(

A Quadrupolar Bis‐Triarylborane Chromophore as a Fluorimetric and Chirooptic Probe for Simultaneous and Selective Sensing of DNA, RNA and Proteins

“…We recently reported the water‐soluble and stable cationic bis‐triarylborane derivative 1 as a new fluorophore applicable for one‐ and two‐photon excited fluorescence imaging in cells . Given that only a few examples of water‐soluble triarylboranes have been reported to date, such borane‐based chromophores could be considered to be novel fluorophores for biochemical applications; they are already widely used in nonlinear optical materials, organic electronics, organic light‐emitting diodes or anion sensors . However, fluorescence of 1 only enabled intracellular localisation of a dye, but did not allow for the determination of a targeted biomacromolecule (for example, protein or DNA or RNA).…”

Synthesis, photophysical and electronic properties of tetra-donor- or acceptor-substitutedortho-perylenes displaying four reversible oxidations or reductions

“…77,78 Diarylboryl groups have attracted much interest for use in optoelectronic materials, as the vacant p z -orbital of the three-coordinate boron serves as a strong p-acceptor, interacting with an adjacent p-system. [79][80][81][82][83][84][85][86][87][88][89][90][91] This conjugation provides the electron-decient character that gives rise to useful photophysical properties. [92][93][94] For example, attaching a Bmes 2 moiety to the 2-and 2,7-positions of pyrene leads to a switch of the energetic order of the LUMO+1 and LUMO, which is a consequence of the mixing of the empty p z -orbital with the pyrene B 3u LUMO+1.…”

Insights into the Optical Properties of Triarylboranes with Strongly Electron‐Accepting Bis(fluoromesityl)boryl Groups: when Theory Meets Experiment

“…A large number of air‐stable conjugated three‐coordinate organoboron compounds have been synthesized over the last few decades for various applications, particularly in linear and nonlinear optics, electro‐optic devices, anion sensors, cell imaging, etc. The boron center in these species possesses an empty p ‐orbital and can thus serve as a strong π‐acceptor following photo‐excitation, or as a readily reducible center.…”