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Design, Synthesis and Optical Properties of 2‐(1‐Azaazulenyl)pyrrole‐Boron Difluoride Complexes

Herein, 1‐azaazulene‐based BF2 complexes with pyrrole as the amido N‐donor were synthesized via Suzuki‐Miyaura cross coupling of 2‐bromo‐1‐azaazulene and 1‐Boc‐2‐pyrroleboronic acid. The structures, especially the unique N–B linkages, were discussed… Click to show full abstract

Herein, 1‐azaazulene‐based BF2 complexes with pyrrole as the amido N‐donor were synthesized via Suzuki‐Miyaura cross coupling of 2‐bromo‐1‐azaazulene and 1‐Boc‐2‐pyrroleboronic acid. The structures, especially the unique N–B linkages, were discussed based on the single crystal analysis and DFT calculations. Compared to the parent BODIPY, the unsubstituted complex 3a exhibited similar absorption maximum and three times larger Stokes shift. The optical properties can be further tuned by introducing aryl substituents at the α‐position of pyrrole moiety.

Keywords: properties azaazulenyl; azaazulenyl pyrrole; synthesis optical; pyrrole boron; design synthesis; optical properties

Journal Title: Asian Journal of Organic Chemistry
Year Published: 2025

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