{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,29]],"date-time":"2026-04-29T11:47:04Z","timestamp":1777463224696,"version":"3.51.4"},"reference-count":27,"publisher":"MDPI AG","issue":"8","license":[{"start":{"date-parts":[[2015,8,13]],"date-time":"2015-08-13T00:00:00Z","timestamp":1439424000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The reactivity of the 2-aryl-4-chloro-6-iodoquinazolines towards palladium catalyzed sequential (Sonogashira\/Suzuki-Miyaura) and one-pot two-step cross-coupling  (bis-Sonogashira, and successive Sonogashira\/Stille) reactions to afford novel unsymmetrical polycarbo-substituted quinazolines has been evaluated. In contrast to the chloro-bromo substituted quinazolines in which selectivity has been previously found to generally favor substitution at the more activated C(4)-Cl bond over the weaker Csp2-Br bond, substitution in the case of the chloro-iodo derivatives favors cross-coupling through the intrinsically more reactive Csp2-I bond. The electronic absorption and emission properties of the prepared  2,3-diaryl-6-(phenylethynyl)quinazolines were studied in solvents of different polarity (dichloromethane, toluene, DMF, methanol) and CH2Cl2-TFA mixture using UV-Vis and emission spectroscopic techniques complemented with density functional theory method to establish the effect of substituents on intramolecular charge transfer properties.<\/jats:p>","DOI":"10.3390\/molecules200814656","type":"journal-article","created":{"date-parts":[[2015,8,13]],"date-time":"2015-08-13T11:13:57Z","timestamp":1439464437000},"page":"14656-14683","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":16,"title":["Synthesis and Photophysical Properties of  Polycarbo-Substituted Quinazolines Derived from the  2-Aryl-4-chloro-6-iodoquinazolines"],"prefix":"10.3390","volume":"20","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-6018-5671","authenticated-orcid":false,"given":"Malose","family":"Mphahlele","sequence":"first","affiliation":[{"name":"Department of Chemistry, College of Science, Engineering and Technology,  University of South Africa, P.O. Box 392, Pretoria 0003, South Africa"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hugues","family":"Paumo","sequence":"additional","affiliation":[{"name":"Department of Chemistry, College of Science, Engineering and Technology,  University of South Africa, P.O. Box 392, Pretoria 0003, South Africa"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8624-8431","authenticated-orcid":false,"given":"Lydia","family":"Rhyman","sequence":"additional","affiliation":[{"name":"Computational Chemistry Group, Department of Chemistry, Faculty of Science,  University of Mauritius, R\u00e9duit 80837, Mauritius"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ponnadurai","family":"Ramasami","sequence":"additional","affiliation":[{"name":"Computational Chemistry Group, Department of Chemistry, Faculty of Science,  University of Mauritius, R\u00e9duit 80837, Mauritius"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2015,8,13]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"6632","DOI":"10.1021\/ja9004927","article-title":"Theoretical bond dissociation energies of halo-heterocycles: Trends and relationships to regioselectivity in palladium-catalyzed cross-coupling reactions","volume":"131","author":"Garcia","year":"2009","journal-title":"J. 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