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Pregled bibliografske jedinice broj: 236351

Časopis

Autori: Basarić, Nikola; Wan, Peter
Naslov: Competing Excited State Intramolecular Proton Transfer (ESIPT) Pathways from Phenol to Anthracene Moieties
Izvornik: The Journal of Organic Chemistry (0022-3263) 71 (2006), 7; 2677-2686
Vrsta rada: članak
Ključne riječi: photochemistry; proton transfer; anthracenes; phenols; quinone methides
Sažetak:
Four new 9-(2’ -hydroxyphenyl)anthracene derivatives 7-10 were synthesized and their potential ESIPT reaction investigated. Whereas 7 reacted via the anticipated (formal) ESIPT reaction (proton transfer to the 10-position of the anthracene), derivatives 8-10 reacted via ESIPT to both 9 and 10-positions, giving rise to two types of intermediates, quinone methides (e.g. 29) and zwitterions (e. g. 30). These intermediates are trapped by solvent (water or methanol) giving addition products that can readily revert back to starting material. However, on extended photolysis, the products that are isolated can best be rationalized as being due to competing elimination and intramolecular cyclization of zwitterions 30 and 37. These results show that it is possible to structurally tune ESIPT in (hydroxyphenyl)anthracenes to either result in a completely reversible reaction or give isolable anthracene addition or rearrangement products.
Projekt / tema: 0098052
Izvorni jezik: ENG
Rad je indeksiran u
bazama podataka:
Current Contents Connect (CCC)
Scopus
SCI-EXP, SSCI i/ili A&HCI
Science Citation Index Expanded (SCI-EXP) (sastavni dio Web of Science Core Collectiona)
Kategorija: Znanstveni
Znanstvena područja:
Kemija
URL Internet adrese: http://pubs.acs.org/journals/joceah/index.html
URL cjelovitog teksta:
Google Scholar: Competing Excited State Intramolecular Proton Transfer (ESIPT) Pathways from Phenol to Anthracene Moieties



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