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Excited state intramolecular proton transfer (ESIPT) in 3-hydroxyanthracene-2-carbaldehyde


Škalamera, Đani; Basarić, Nikola; Mlinarić-Majerski, Kata; Wan, Peter
Excited state intramolecular proton transfer (ESIPT) in 3-hydroxyanthracene-2-carbaldehyde // e-WISPOC 2013 / 2nd Training School COST Action CM1005 Supremolecular Chemistry in Water
Bressanone, Italia, 2013. str. 622-P86 (poster, međunarodna recenzija, sažetak, ostalo)


Naslov
Excited state intramolecular proton transfer (ESIPT) in 3-hydroxyanthracene-2-carbaldehyde

Autori
Škalamera, Đani ; Basarić, Nikola ; Mlinarić-Majerski, Kata ; Wan, Peter

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, ostalo

Izvornik
E-WISPOC 2013 / 2nd Training School COST Action CM1005 Supremolecular Chemistry in Water / - Bressanone, Italia, 2013, 622-P86

Skup
E-WISPOC 2013 / 2nd Training School COST Action CM1005 Supremolecular Chemistry in Water

Mjesto i datum
Bressanone, Italia, 27.01-01.02.2013

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
Proton transfer; ESIPT; anthracene carbaldehyde; anthrol derivative

Sažetak
Upon electronic excitation, some organic functional groups exhibit enhanced acidity or basicity. If these groups are in close proximity, an excited-state intramolecular proton transfer (ESIPT) can occur. ESIPT has been the focus of intensive research in the last four decades because of its fundamental importance, as well as many applications, including sensing, photolabeling, laser dyes, photostabilizers, scintilators, photoswitching in fluorescent proteins, long-lived pH jumps or switching polymorphs.[1] Among the first examples of ESIPT was the one reported for salicylaldehyde (1) in which the large-Stokes shifted emission from the photo-tautomer 2 was observed.[2] Investigation of ESIPT has also recently been extended to larger naphthalene chromophoric systems 3-5.[3] However, to date, experimental evidence of ESIPT in the anthracene carbaldehyde derivatives has not been reported. Within the on-going project in our laboratory concerning the investigation of various ESIPT systems [4], we have prepared 3-hydroxyanthracene-2-carbaldehyde (6) and investigated its photochemical reactivity. ESIPT process was investigated by fluorescence, laser flash photolysis, and ab initio calculations. Herein, we report the first example of direct ESIPT in the anthrol derivative which is of particular interest since it can be faciliated by light of longer wavelenghts (350-400 nm), and therefore has many potential applications.

Izvorni jezik
Engleski



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