Photochemical [2+2] cycloadditions of naphthalene acrylic acids: templated and untemplated photoreactivity, selective homo/heterodimerizations, and conformational analysis

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dc.contributor.authorTemel, Merve
dc.contributor.authorYildiz, Gizem
dc.contributor.authorCeyhan, Kaan Berkay
dc.contributor.authorAlkan, Fahri
dc.contributor.authorSahin, Onur
dc.contributor.authorTurkmen, Yunus E.
dc.date.accessioned2026-04-25T14:20:05Z
dc.date.available2026-04-25T14:20:05Z
dc.date.issued2025
dc.departmentSinop Üniversitesi
dc.description.abstractSelective homo- and heterodimerization reactions of naphthalene acrylic acids have been achieved in a diastereocontrolled manner with the use of 1,8-dihydroxynaphthalene as a covalent template in photochemical [2 + 2] cycloadditions. When the reactions were run in solution, cycloaddition products were obtained in good yields (64-88%), which were subsequently detached from the template via a transesterification reaction affording the symmetrical and unsymmetrical cyclobutane products in 75-91% yields. A careful examination of the crystal structures of diester 6a and cycloadduct 15a along with detailed powder XRD and ATR-IR spectroscopic studies revealed an intriguing case of conformational isomerism in 15a arising from the different possible orientations of its two ester carbonyls. The rotational barriers between the different conformers of 15a were calculated to be within the range of 4.19-7.10 kcal mol-1, indicative of rapid interconversion between these conformers in solution at room temperature.
dc.description.sponsorshipGEBIP Award of the Turkish Academy of Sciences
dc.description.sponsorshipThe numerical calculations reported in this article were fully performed at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA resources). Y. E. T. acknowledges financial support by the GEBIP Award of the Turkish Academy of Sciences. The authors also acknowledge the Scientific and Technological Research Application and Research Center, Sinop University, Turkiye, for the use of the Bruker D8 Quest diffractometer.
dc.identifier.doi10.1039/d5ra03698d
dc.identifier.endpage24556
dc.identifier.issn2046-2069
dc.identifier.issue30
dc.identifier.orcid0009-0001-5828-2384
dc.identifier.orcid0000-0002-9797-2820
dc.identifier.orcid0000-0002-4046-9044
dc.identifier.orcid0009-0008-3461-8796
dc.identifier.orcid0009-0007-5788-2250
dc.identifier.orcid0000-0003-3765-3235
dc.identifier.pmid40661196
dc.identifier.scopus2-s2.0-105010694198
dc.identifier.scopusqualityQ1
dc.identifier.startpage24544
dc.identifier.urihttps://doi.org/10.1039/d5ra03698d
dc.identifier.urihttps://hdl.handle.net/11486/8350
dc.identifier.volume15
dc.identifier.wosWOS:001527438700001
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherRoyal Soc Chemistry
dc.relation.ispartofRsc Advances
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/openAccess
dc.snmzKA_WOS_20260420
dc.subject#BAŞV!
dc.titlePhotochemical [2+2] cycloadditions of naphthalene acrylic acids: templated and untemplated photoreactivity, selective homo/heterodimerizations, and conformational analysis
dc.typeArticle

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