TY - JOUR
T1 - Synthesis, electrochemical/photophysical properties and computational investigation of 3,5-dialkyl BODIPY fluorophores
AU - Derin, Yavuz
AU - Yılmaz, Raşit Fikret
AU - Baydilek, İbrahim Halil
AU - Atalay, Vildan Enisoğlu
AU - Özdemir, Abdil
AU - Tutar, Ahmet
N1 - Publisher Copyright:
© 2018 Elsevier B.V.
PY - 2018/10/1
Y1 - 2018/10/1
N2 - A series of 3,5 dimethyl and diethyl BODIPY with different substitutions at meso position are synthesized and characterized. Photophysical and electrochemical features of the 3,5 dialkyl BODIPY fluorophores are investigated using experimental and computational approaches. All fluorophores display absorption maxima around at 510 nm and emission maxima around at 520 nm which correspound to very narrow Stokes shift. Among the fluorophores, 3,5,8 alkylated BODIPYs are found to have high fluorescence quantum yield (1.00–0.93). 4-Bromophenyl group at meso position decreases fluorescence quantum yield of the dye while it increases with 4-methoxyphenyl group at meso position. The HOMO-LUMO energies of synthesized fluorophore compounds were calculated by B3LYP/6-31G(d,p) and B3LYP/6-311+G(d,p) levels in chloroform phase. Electron donating and accepting groups show increasing and decreasing effect on the band gaps of the fluorophores respectively.
AB - A series of 3,5 dimethyl and diethyl BODIPY with different substitutions at meso position are synthesized and characterized. Photophysical and electrochemical features of the 3,5 dialkyl BODIPY fluorophores are investigated using experimental and computational approaches. All fluorophores display absorption maxima around at 510 nm and emission maxima around at 520 nm which correspound to very narrow Stokes shift. Among the fluorophores, 3,5,8 alkylated BODIPYs are found to have high fluorescence quantum yield (1.00–0.93). 4-Bromophenyl group at meso position decreases fluorescence quantum yield of the dye while it increases with 4-methoxyphenyl group at meso position. The HOMO-LUMO energies of synthesized fluorophore compounds were calculated by B3LYP/6-31G(d,p) and B3LYP/6-311+G(d,p) levels in chloroform phase. Electron donating and accepting groups show increasing and decreasing effect on the band gaps of the fluorophores respectively.
KW - BODIPY
KW - DFT
KW - Fluorescence quantum yield
KW - HOMO-LUMO
UR - http://www.scopus.com/inward/record.url?scp=85048293741&partnerID=8YFLogxK
U2 - 10.1016/j.ica.2018.06.006
DO - 10.1016/j.ica.2018.06.006
M3 - Article
AN - SCOPUS:85048293741
SN - 0020-1693
VL - 482
SP - 130
EP - 135
JO - Inorganica Chimica Acta
JF - Inorganica Chimica Acta
ER -