{"title":"Design and synthesis of a 2,5-Diarylthiophene chromophore for enhanced near-infrared two-photon uncaging efficiency of calcium ions","authors":"Tam Thi Thanh Tran, Manabu Abe","doi":"10.1007/s43630-024-00623-5","DOIUrl":null,"url":null,"abstract":"<p>The design and synthesis of two-photon-responsive chromophores have recently garnered significant attention owing to their potential applications in materials and life sciences. In this study, a novel π-conjugated system, 2-dimethylaminophenyl-5-nitrophenylthiophene derivatives, featuring a thiophene unit as the π-linker between the donor (NMe<sub>2</sub>C<sub>6</sub>H<sub>4</sub>–) and acceptor (NO<sub>2</sub>C<sub>6</sub>H<sub>4</sub>–) units was designed, synthesized, and applied for the development of two-photon-responsive chromophores as a photoremovable protecting group in the near-infrared region. Notably, the positional effect of the nitro group (NO<sub>2</sub>), <i>meta</i> versus <i>para</i> position, was observed in the uncaging process of benzoic acid. Additionally, while the <i>para</i>-isomer exhibited a single fluorescence peak, a dual emission was detected for the <i>meta</i>-isomer in polar solvents. The caged calcium ion (Ca<sup>2+</sup>) incorporating the newly synthesized thiophene unit exhibited a sizable two-photon absorption cross-section value (σ<sub>2</sub> = 129 GM at 830 nm). Both one-photon and two-photon photoirradiation of caged calcium ions successfully released calcium ions, indicating the potential utility of 2,5-diarylthiophene derivatives in future biological studies.</p><h3 data-test=\"abstract-sub-heading\">Graphical abstract</h3>","PeriodicalId":98,"journal":{"name":"Photochemical & Photobiological Sciences","volume":"6 1","pages":""},"PeriodicalIF":2.7000,"publicationDate":"2024-09-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Photochemical & Photobiological Sciences","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1007/s43630-024-00623-5","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
引用次数: 0
Abstract
The design and synthesis of two-photon-responsive chromophores have recently garnered significant attention owing to their potential applications in materials and life sciences. In this study, a novel π-conjugated system, 2-dimethylaminophenyl-5-nitrophenylthiophene derivatives, featuring a thiophene unit as the π-linker between the donor (NMe2C6H4–) and acceptor (NO2C6H4–) units was designed, synthesized, and applied for the development of two-photon-responsive chromophores as a photoremovable protecting group in the near-infrared region. Notably, the positional effect of the nitro group (NO2), meta versus para position, was observed in the uncaging process of benzoic acid. Additionally, while the para-isomer exhibited a single fluorescence peak, a dual emission was detected for the meta-isomer in polar solvents. The caged calcium ion (Ca2+) incorporating the newly synthesized thiophene unit exhibited a sizable two-photon absorption cross-section value (σ2 = 129 GM at 830 nm). Both one-photon and two-photon photoirradiation of caged calcium ions successfully released calcium ions, indicating the potential utility of 2,5-diarylthiophene derivatives in future biological studies.
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