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However, these relationships are difficult to decipher, as the crystal packing affects both the intermolecular interactions and the molecular conformation. Here, we report a divergent synthetic strategy to generate a family of rigid carbonyl\u2010bridged triphenylamine (TPA)\u2010based chromophores via metal\u2010free transformations of the same starting material, and exploit this family to investigate the effects of crystal packing on the solid state RTP properties. The minor bridge modifications lead the TPA derivatives to adopt three distinct crystal packing motifs: parallel columnar stacks, antiparallel zigzags, and nonparallel dimerized arrangements. Despite the nearly identical RTP spectra across the series, the proportion of phosphorescence in their emission and the RTP lifetimes are shown to differ as a result of the different crystal motifs. Computational investigations of dimer models of the solid state reveal that the interplay between fluorescence and triplet formation can be modelled by identifying the aggregate character of dimers in the crystal, but only if pairs in multiple dimensions of the crystal are considered.<\/jats:p>","DOI":"10.1002\/anie.202512446","type":"journal-article","created":{"date-parts":[[2025,8,1]],"date-time":"2025-08-01T06:26:49Z","timestamp":1754029609000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":17,"title":["Divergent Synthesis and Crystal Engineering of Room\u2010Temperature Phosphorescent Carbonyl\u2010Bridged Triphenylamines"],"prefix":"10.1002","volume":"64","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3520-6995","authenticated-orcid":false,"given":"Cory","family":"Ruchlin","sequence":"first","affiliation":[{"name":"Department of Chemistry McGill University  801 Sherbrooke Street West Montreal Quebec H3A 0B8 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1309-6366","authenticated-orcid":false,"given":"Durbis J.","family":"Castillo\u2010Pazos","sequence":"additional","affiliation":[{"name":"Department of Chemistry McGill University  801 Sherbrooke Street West Montreal Quebec H3A 0B8 Canada"},{"name":"FRQNT Centre for Green Chemistry and Catalysis McGill University  Montreal Quebec H3A 0B8 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8835-4051","authenticated-orcid":false,"given":"Juan D.","family":"Lasso","sequence":"additional","affiliation":[{"name":"Department of Chemistry McGill University  801 Sherbrooke Street West Montreal Quebec H3A 0B8 Canada"},{"name":"FRQNT Centre for Green Chemistry and Catalysis McGill University  Montreal Quebec H3A 0B8 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5427-9444","authenticated-orcid":false,"given":"Ehsan","family":"Hamzehpoor","sequence":"additional","affiliation":[{"name":"Department of Chemistry McGill University  801 Sherbrooke Street West Montreal Quebec H3A 0B8 Canada"},{"name":"D\u00e9partement de Chimie Institut Courtois Universit\u00e9 de Montr\u00e9al  1375 Avenue Th\u00e9r\u00e8se\u2010Lavoie\u2010Roux Montr\u00e9al Qu\u00e9bec H2V 0B3 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0001-1400-282X","authenticated-orcid":false,"given":"Aleksandar","family":"Mikov","sequence":"additional","affiliation":[{"name":"Department of Chemistry McGill University  801 Sherbrooke Street West Montreal Quebec H3A 0B8 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3859-8824","authenticated-orcid":false,"given":"Chao\u2010Jun","family":"Li","sequence":"additional","affiliation":[{"name":"Department of Chemistry McGill University  801 Sherbrooke Street West Montreal Quebec H3A 0B8 Canada"},{"name":"FRQNT Centre for Green Chemistry and Catalysis McGill University  Montreal Quebec H3A 0B8 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2233-416X","authenticated-orcid":false,"given":"Dmytro F.","family":"Perepichka","sequence":"additional","affiliation":[{"name":"Department of Chemistry McGill University  801 Sherbrooke Street West Montreal Quebec H3A 0B8 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,7,31]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41566-022-00958-4"},{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/adom.202001549"},{"key":"e_1_2_8_3_1","first-page":"1391","volume":"3","author":"Yang J.","year":"2019","journal-title":"Chem. 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