BOPAM: Efficient Synthesis of a Bright Asymmetric Bis‐Boron Complex and its Dark Side
Jianjun Huang, Flip de Jong, Davita Martina Elisa van Raamsdonk, Jonathan Vandenwijngaerden, Akane Inoue, Daniel Escudero, Luc Van Meervelt, Mark Van der Auweraer, Wim Dehaen- Atomic and Molecular Physics, and Optics
- Electronic, Optical and Magnetic Materials
Abstract
A new family of unsymmetrical boron chromophores chelated with two BF2 units, named BOPAM, has been developed via a one‐pot, three‐step reaction starting from commercially available thioamides via i) conversion to amidrazones, ii) condensation with pyrrole aldehydes, and iii) boron chelation. This synthetic pathway has been proven to be highly efficient, having a broad substrate tolerance and giving the BOPAM products high yield. Notably, some of the BOPAM dyes show interesting photophysical properties with fluorescence quantum yields up to 0.98 in toluene. A fine‐tuning of their emissive properties has been attained through tailored molecular design strategies guided by in‐depth computational investigations. Tailored substitution with electron‐donating groups at the BOPAM ring leads to the opening of a non‐radiative decay channel involving a dark state and consequently a significant quenching of the fluorescence. The study is complemented by exhaustive steady‐state and time‐resolved spectroscopic measurements.