Triphenylamine/4,4′-Dimethoxytriphenylamine-Functionalized Thieno[3,2-b]thiophene Fluorophores with a High Quantum Efficiency: Synthesis and Photophysical Properties

Recep Isci; Melis Unal; Gizem Kucukcakir; Naime A. Gurbuz; Sultan F. Gorkem; Turan Ozturk

doi:10.1021/acs.jpcb.1c09448

Triphenylamine/4,4′-Dimethoxytriphenylamine-Functionalized Thieno[3,2-b]thiophene Fluorophores with a High Quantum Efficiency: Synthesis and Photophysical Properties

Recep Isci
, Melis Unal
, Gizem Kucukcakir
, Naime A. Gurbuz
, Sultan F. Gorkem
, Turan Ozturk^*

^*Corresponding author for this work

Department of Chemistry

Istanbul Technical University
Eskisehir Technical University
Scientific and Technological Research Council of Turkey

Research output: Contribution to journal › Article › peer-review

43 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	13309-13319
Number of pages	11
Journal	Journal of Physical Chemistry B
Volume	125
Issue number	48
DOIs	https://doi.org/10.1021/acs.jpcb.1c09448
Publication status	Published - 9 Dec 2021

Bibliographical note

Publisher Copyright:
© 2021 American Chemical Society

Funding

The authors thank Higher Education Council of Turkey (YOK) and TUBITAK grants to Recep Isci (Ph.D., 100/2000 YOK and 2211A BIDEP/TUBITAK), 214Z297 numbered British Council TUBITAK Project, and Unsped Global Lojistik, Turkey, for financial support.

Funders	Funder number
British Council TUBITAK Project
Higher Education Council of Turkey	214Z297, 2211A BIDEP/TUBITAK, 100/2000 YOK

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10.1021/acs.jpcb.1c09448

Cite this

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title = "Triphenylamine/4,4′-Dimethoxytriphenylamine-Functionalized Thieno[3,2-b]thiophene Fluorophores with a High Quantum Efficiency: Synthesis and Photophysical Properties",

abstract = "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.",

author = "Recep Isci and Melis Unal and Gizem Kucukcakir and Gurbuz, \{Naime A.\} and Gorkem, \{Sultan F.\} and Turan Ozturk",

note = "Publisher Copyright: {\textcopyright} 2021 American Chemical Society",

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doi = "10.1021/acs.jpcb.1c09448",

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Triphenylamine/4,4′-Dimethoxytriphenylamine-Functionalized Thieno[3,2-b]thiophene Fluorophores with a High Quantum Efficiency: Synthesis and Photophysical Properties. / Isci, Recep; Unal, Melis; Kucukcakir, Gizem et al.
In: Journal of Physical Chemistry B, Vol. 125, No. 48, 09.12.2021, p. 13309-13319.

Research output: Contribution to journal › Article › peer-review

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

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.

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Triphenylamine/4,4′-Dimethoxytriphenylamine-Functionalized Thieno[3,2-b]thiophene Fluorophores with a High Quantum Efficiency: Synthesis and Photophysical Properties

Abstract

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