DOI: 10.1021/acs.orglett.6c03789 ISSN: 1523-7060
Design of Small Circularly Polarized Luminescence-Active Planar-Chiral Azaboroles
Jakub Koudelka, Timothée Cadart, Ivana Císařová, Róbert Gyepes, Miroslav Štěpánek, Jan Fischer, Jhon Sebastian Oviedo Ortiz, Jeanne Crassous, Martin KotoraAbstract
We report an enantioselective approach toward new planar-chiral azaboroles bearing the [2.2]paracyclophane unit and studies of their (chir)optical properties. Fusing the planar-chiral scaffold with a B,N-heterocycle led to the formation of a set of three substances, all of which have interesting chiroptical properties (glum up to 4.7 × 10–3 and BCPL up to 3.1 M–1 cm–1). 1a exhibits superior fluorescence in the solid state unlike the rest of the series.