Naslov
Competing Excited State Intramolecular Proton Transfer (ESIPT) Pathways from Phenol to Anthracene Moieties

Autori
Basarić, Nikola ; Wan, Peter

Izvornik
The Journal of Organic Chemistry (0022-3263) 71 (2006), 7; 2677-2686

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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