Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 8, Pages 3959-3968Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo3003216
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Funding
- FCT (Portugal's Foundation for Science and Technology)
- Fonds Europeens de Developpement Regional (FEDER) research unit Centro de Quimica-Vila Real [POCTI-SFA-3-616]
- Region Nord-Pas de Calais (France)
- Ministere de la Jeunesse de l'Education Nationale et de la Recherche (MJENR)
- [PTDC/QUI/66012/2006]
- Fundação para a Ciência e a Tecnologia [PTDC/QUI/66012/2006] Funding Source: FCT
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A series of new photochromic fused-naphthopyrans with an alkyl bridge between the pyran ring and the naphthalenic core was synthesized in several steps from 4-(bromomethyl)benzocoumarin. The presence of the alkyl bridge in these new fused-naphthopyrans prevents the formation of one long-lived photoisomer and therefore has a dramatic effect on their photochromic properties: UV irradiation of common naphthopyrans gives rise to two isomeric colored photoisomers, one of which fades very slowly and is responsible for a persistent residual color. UV excitation of these new uncolored fused-naphthopyrans leads to the formation of only one colored photoisomer that fades completely to the uncolored state in few seconds/minutes following a monoexponential decay law, thus avoiding the problem of the residual coloration typically observed with naphthopyrans.
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