TY - JOUR
T1 - Triphenylamine/4,4′-Dimethoxytriphenylamine-Functionalized Thieno[3,2-b]thiophene Fluorophores with a High Quantum Efficiency
T2 - Synthesis and Photophysical Properties
AU - Isci, Recep
AU - Unal, Melis
AU - Kucukcakir, Gizem
AU - Gurbuz, Naime A.
AU - Gorkem, Sultan F.
AU - Ozturk, Turan
N1 - Publisher Copyright:
© 2021 American Chemical Society
PY - 2021/12/9
Y1 - 2021/12/9
N2 - A wide series of 10 new triphenylamine (TPA)/4,4′-dimethoxytriphenylamine (TPA(OMe)2)-functionalized thieno[3,2-b]thiophene (TT) fluorophores,4a-eand5a-e, bearing different electron-donating and electron-withdrawing substituents (-PhCN, -PhF, -PhOMe, -Ph, and -C6H13) at the terminal thienothiophene units were designed and synthesized by the Suzuki coupling reaction. Their optical and electrochemical properties were investigated by experimental and computational studies. Solid-state fluorescent quantum yields were recorded to be from 20 to 69%, and the maximum solution-state quantum efficiency reached 97%. Moreover, the photophysical characterization of the novel chromophores demonstrated a significant Stokes shift, reaching 179 nm with a bathochromic shift. They exhibited tuning color emission from orange to dark blue in solution and showed fluorescence lifetime reaching 4.70 ns. The relationship between triphenylamine (TPA)/4,4′-dimethoxytriphenylamine (TPA(OMe)2)-derived triarylamines and different functional groups on thieno[3,2-b] thiophene units was discussed.
AB - A wide series of 10 new triphenylamine (TPA)/4,4′-dimethoxytriphenylamine (TPA(OMe)2)-functionalized thieno[3,2-b]thiophene (TT) fluorophores,4a-eand5a-e, bearing different electron-donating and electron-withdrawing substituents (-PhCN, -PhF, -PhOMe, -Ph, and -C6H13) at the terminal thienothiophene units were designed and synthesized by the Suzuki coupling reaction. Their optical and electrochemical properties were investigated by experimental and computational studies. Solid-state fluorescent quantum yields were recorded to be from 20 to 69%, and the maximum solution-state quantum efficiency reached 97%. Moreover, the photophysical characterization of the novel chromophores demonstrated a significant Stokes shift, reaching 179 nm with a bathochromic shift. They exhibited tuning color emission from orange to dark blue in solution and showed fluorescence lifetime reaching 4.70 ns. The relationship between triphenylamine (TPA)/4,4′-dimethoxytriphenylamine (TPA(OMe)2)-derived triarylamines and different functional groups on thieno[3,2-b] thiophene units was discussed.
UR - http://www.scopus.com/inward/record.url?scp=85120376491&partnerID=8YFLogxK
U2 - 10.1021/acs.jpcb.1c09448
DO - 10.1021/acs.jpcb.1c09448
M3 - Article
C2 - 34807616
AN - SCOPUS:85120376491
SN - 1520-6106
VL - 125
SP - 13309
EP - 13319
JO - Journal of Physical Chemistry B
JF - Journal of Physical Chemistry B
IS - 48
ER -