Pyrrolylquinoline-BF2 and BPh2 BODIPY-Type Analogues: Synthesis, Structural Analysis and Photophysical Properties

Autor: Abdulrahman A. Alsimaree, Omar M. Alatawi, Paul G. Waddell, David P. Day, Nawaf I. Alsenani, Julian G. Knight
Jazyk: angličtina
Rok vydání: 2021
Předmět:
Zdroj: Crystals, Vol 11, Iss 9, p 1103 (2021)
Druh dokumentu: article
ISSN: 2073-4352
DOI: 10.3390/cryst11091103
Popis: Two new pyrrolylquinoline-substituted heteroaromatic-containing compounds bearing a central boron bridge have been prepared by a short, high-yielding sequence consisting of Suzuki-coupling of 8-bromoquinoline and N-Boc 2-pyrroleboronic acid, thermolytic tert-butyloxycarbonyl deprotection, and subsequent boron chelation (either using boron trifluoride or triphenylborane). Both derivatives display longer wavelength absorption maxima (λabsmax) than a previously reported indolopyridine-BPh2 analogue, in agreement with the smaller HOMO-LUMO energy gap predicted by DFT quantum chemical calculations. Both of the pyrrolylquinoline-boron chelates display weak emission (quantum yields 0.3–0.9%) and the BPh2 complex displays a very broad, long-wavelength emission (λemmax = 715 nm, MeCN), which may be due to dimer emission and results in a large pseudo-Stokes’ shift (7753 cm−1) for this compound.
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