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This research focuses on the synthesis and characterization of a novel stable dicarbatriphyrin(2.1.1) which was constructed by amending the [14]triphyrin(2.1.1) framework by, replacing two pyrrole rings with <jats:italic>meta<\/jats:italic>\u2010connected phenyl rings and introducing an <jats:italic>o<\/jats:italic>\u2010benzene bridge at the C2 position. The structural modification resulted in a saddle\u2010shaped macrocyclic core with negative Gaussian curvature, as confirmed by crystal structure analysis. This unique molecular topology offers acumens into the structure\u2010property relationships in the curved locally \u03c0\u2010conjugated contracted porphyrinoids. The macrocycle exhibits fluorescent emission in solution, which is selectively quenched by Fe(III) ions, highlighting its potential as a chemosensor for Fe(III) cations. Additionally, the formation of carbacalix[1]phyrin(<jats:bold>2<\/jats:bold>.<jats:italic>1.1<\/jats:italic>), a phlorin analogue of dicarbatriphyrin(2.1.1), which exhibits a chair conformation in contrast to the saddle\u2010shaped structure of its oxidized counterpart. Remarkably, the emergence of a mono\u2010pyrrolic calixbenziphyrin marks an unprecedented advancement in the field of calixphyrin chemistry. Moreover, theoretical studies provide strong support for the experimental findings, reinforcing the conclusions drawn from the structural and functional analyses.<\/jats:p>","DOI":"10.1002\/asia.202401089","type":"journal-article","created":{"date-parts":[[2024,10,7]],"date-time":"2024-10-07T16:08:31Z","timestamp":1728317311000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Dicarbatriphyrin(2.1.1) and its Carbacalix[1]Phyrin Analogue: Structure\u2010Property Relationships and Application as a Fe(III) Chemosensor"],"prefix":"10.1002","volume":"20","author":[{"given":"Adrija","family":"Kayal","sequence":"first","affiliation":[{"name":"School of Chemical Sciences National Institute of Science Education and Research (NISER) An OCC of Homi Bhabha National Institute  Bhubaneswar 752050, Odisha India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sourav","family":"Ranjan Pradhan","sequence":"additional","affiliation":[{"name":"School of Chemical Sciences National Institute of Science Education and Research (NISER) An OCC of Homi Bhabha National Institute  Bhubaneswar 752050, Odisha India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chetan","family":"Kumar Prasad","sequence":"additional","affiliation":[{"name":"School of Chemical Sciences National Institute of Science Education and Research (NISER) An OCC of Homi Bhabha National Institute  Bhubaneswar 752050, Odisha India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mainak","family":"Das","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of York, Heslington  York YO10 5DD UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8467-1538","authenticated-orcid":false,"given":"A.","family":"Srinivasan","sequence":"additional","affiliation":[{"name":"School of Chemical Sciences National 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