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Photoisomerizations of the photochromic anil salicylidene-1-naphthylamine in 3-methylpentane

✍ Scribed by J.S. Stephan; A. Mordziński; C.Ríos Rodríguez; K.H. Grellmann

Publisher
Elsevier Science
Year
1994
Tongue
English
Weight
852 KB
Volume
229
Category
Article
ISSN
0009-2614

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✦ Synopsis

The results of a nanosecond flash-photolysis study with solutions of salicylidene-1-naphthyl-amine (SN) in 3-methylpentane (3MP) at ambient and at low temperatures are reported. Besides a newly discovered triplet state, two photochromic transients (PCTs) are formed after excited state intramolecular proton-transfer (ESIPT) has taken place. Above 140 K the formation of a quinoid trans-keto tautomer ( 'K,,) prevails. .4t 100 K a second PCT is observed in steady-state experiments which we tentatively assign to a twisted conformer of the keto form of SN. The transient 'Ktr re-enolizes in dry 3MP by second-order double proton-transfer; in the presence of 10m4 M methanol the re-enolization of 'K,, is proton catalyzed and the lifetime of 'K,, is shortened by more than two orders of magnitude. The properties of the flexible SN are compared with two other rotationally hindered 'ESIPT molecules'.

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