Optoelectronic Properties of Carbon-Bound Boron Difluoride Hydrazone Dimers.
CHEMISTRY-A EUROPEAN JOURNAL(2020)
摘要
The creation of dimeric boron difluoride complexes of chelating N-donor ligands is a proven strategy for the enhancement of the optoelectronic properties of fluorescent dyes. We report dimers based on the boron difluoride hydrazone (BODIHY) framework, which offer unique and sometimes unexpected substituent-dependent absorption, emission, and electrochemical properties. BODIHY dimers have low-energy absorption bands (lambda(max)=421 to 479 nm, epsilon=17 200 to 39 900 m(-1) cm(-1)) that are red-shifted relative to monomeric analogues. THF solutions of these dimers exhibit aggregation-induced emission upon addition of water, with emission enhancement factors ranging from 5 to 18. Thin films of BODIHY dimers are weakly emissive as a result of the inner-filter effect, attributed to intermolecular pi-type interactions. BODIHY dimers are redox-active and display two one-electron oxidation and two one-electron reduction waves that strongly depend on the N-aryl substituents. These properties are rationalized using density-functional theory calculations and X-ray crystallography experiments.
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关键词
aggregation-induced emission,boron-nitrogen heterocycles,cyclic voltammetry,electronic structure calculations,X-ray crystallography
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