Alkynylboration Reaction Leading to Boron-Containing π-Extended <i>cis</i>-Stilbenes as a Highly Tunable Fluorophore

Marina Nogami, Keiichi Hirano, Kensuke Morimoto, Masaru Tanioka, Kazunori Miyamoto, Atsuya Muranaka, Masanobu Uchiyama

Organic Letters · 2019 · 33 citations · 31 references

Concepts

Abstract

An unprecedented boron-containing fluorophore, π-extended cis-stilbene, obtained via alkynylboration reaction of alkynamide is reported. Boron-containing π-extended cis-stilbenes emit fluorescence with high quantum yields in the solid state and exhibit aggregation-induced emission enhancement. The broad substrate scope of the alkynylboration reaction offers facile access to electronically diverse structures, enabling fine-tuning of light absorption/emission characteristics. The boron-containing π-extended cis-stilbene with a diphenylamino group displays solvatofluorochromism via an intramolecular charge-transfer transition.

References

31