Synthesis and Properties of Thiophene-Quinone Helicenes with Different Molecular Curvature
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Issued Date
2025-01-01
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ISSN
18614728
eISSN
1861471X
Scopus ID
2-s2.0-85218917167
Journal Title
Chemistry - An Asian Journal
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SCOPUS
Bibliographic Citation
Chemistry - An Asian Journal (2025)
Suggested Citation
Unjaroen D., Hashmi Y., Tananchayakul P., Thongpanchang T. Synthesis and Properties of Thiophene-Quinone Helicenes with Different Molecular Curvature. Chemistry - An Asian Journal (2025). doi:10.1002/asia.202401588 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/105541
Title
Synthesis and Properties of Thiophene-Quinone Helicenes with Different Molecular Curvature
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Abstract
Naphthothiophene-quinone helicenes with different molecular curvatures, i. e., NTQ, 2,3-NDTQ and 2,6-NDTQ, are synthesized in seven steps. Diels−Alder reaction between p-benzoquinone and silyl enol ether derived from the corresponding naphthothiophenes was used as a key step. Both UV-Vis and fluorescence spectroscopy, cyclic voltammetry experiments, including DFT calculation demonstrated that, in comparison to the basic thiophene-quinone system, both M-shaped (2,3-NDTQ) and S-shaped (2,6-NDTQ) structures possessed a narrower HOMO−LUMO band gap than C-shaped NTQ, implying the effect of extended conjugation. The change of molecular shape resulted in the shift in both UV-Vis and fluorescence spectra, but the strong electron withdrawing effect of benzoquinone is more dominant.