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

Crystals

Abdulrahman A. Alsimaree¹  Nawaf I. Alsenani²  Paul G. Waddell³  Omar M. Alatawi³  Julian G. Knight³  David P. Day⁴ 

[1] Department of Basic Science (Chemistry) College of Science and Humanities, Shaqra University, Afif, P.O. Box 33, Shaqra 11961, Saudi Arabia;Department of Chemistry, Faculty of Science, University of AlBaha, Alagig 65779-7738, Saudi Arabia;School of Natural and Environmental Sciences, Bedson Building, Newcastle University, Newcastle upon Tyne NE1 7RU, UK;São Carlos Institute of Chemistry, University of São Paulo, São Carlos 13560-970, SP, Brazil;

关键词: fluorescent molecules;    structural analysis;    boron bridged complex;    DFT analysis;    X-ray crystal analysis;   

DOI  :  10.3390/cryst11091103

来源: DOAJ

【 摘 要 】

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 (λ^abs_max) 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 (λ^em_max = 715 nm, MeCN), which may be due to dimer emission and results in a large pseudo-Stokes’ shift (7753 cm⁻¹) for this compound.

【 授权许可】

Unknown