TY - JOUR
T1 - Pyrrolylquinoline-BF2 and BPh2 BODIPY-type analogues
T2 - Synthesis, structural analysis and photophysical properties
AU - Alsimaree, Abdulrahman A.
AU - Alatawi, Omar M.
AU - Waddell, Paul G.
AU - Day, David P.
AU - Alsenani, Nawaf I.
AU - Knight, Julian G.
N1 - Funding Information:
A.A.A. wishes to thank Newcastle University and Shaqra University for funding and support. O.M.A. thanks Newcastle University and Tabuk University for support.
Publisher Copyright:
© 2021 by the authors. Licensee MDPI, Basel, Switzerland.
PY - 2021/9
Y1 - 2021/9
N2 - 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 (λabs 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 (λem 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.
AB - 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 (λabs 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 (λem 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.
KW - Boron bridged complex
KW - DFT analysis
KW - Fluorescent molecules
KW - Structural analysis
KW - X-ray crystal analysis
UR - http://www.scopus.com/inward/record.url?scp=85114816057&partnerID=8YFLogxK
U2 - 10.3390/cryst11091103
DO - 10.3390/cryst11091103
M3 - Article
AN - SCOPUS:85114816057
VL - 11
JO - Crystals
JF - Crystals
IS - 9
M1 - 1103
ER -