{"title":"Synthesis and Properties of Thiophene-Quinone Helicenes with Different Molecular Curvature","authors":"Duenpen Unjaroen, Yuttawat Hashmi, Pichayut Tananchayakul, Tienthong Thongpanchang","doi":"10.1002/asia.202401588","DOIUrl":null,"url":null,"abstract":"<p>Naphthothiophene-quinone helicenes with different molecular curvatures, <i>i. e</i>., <b>NTQ</b>, <b>2,3-NDTQ</b> and <b>2,6-NDTQ</b>, are synthesized in seven steps. Diels−Alder reaction between <i>p</i>-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 (<b>2,3-NDTQ</b>) and S-shaped (<b>2,6-NDTQ</b>) structures possessed a narrower HOMO−LUMO band gap than C-shaped <b>NTQ</b>, 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.</p>","PeriodicalId":145,"journal":{"name":"Chemistry - An Asian Journal","volume":"20 9","pages":""},"PeriodicalIF":3.3000,"publicationDate":"2025-02-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/asia.202401588","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemistry - An Asian Journal","FirstCategoryId":"1","ListUrlMain":"https://aces.onlinelibrary.wiley.com/doi/10.1002/asia.202401588","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
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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.
期刊介绍：
Chemistry—An Asian Journal is an international high-impact journal for chemistry in its broadest sense. The journal covers all aspects of chemistry from biochemistry through organic and inorganic chemistry to physical chemistry, including interdisciplinary topics.
Chemistry—An Asian Journal publishes Full Papers, Communications, and Focus Reviews.
A professional editorial team headed by Dr. Theresa Kueckmann and an Editorial Board (headed by Professor Susumu Kitagawa) ensure the highest quality of the peer-review process, the contents and the production of the journal.
Chemistry—An Asian Journal is published on behalf of the Asian Chemical Editorial Society (ACES), an association of numerous Asian chemical societies, and supported by the Gesellschaft Deutscher Chemiker (GDCh, German Chemical Society), ChemPubSoc Europe, and the Federation of Asian Chemical Societies (FACS).
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