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Synthesis of 1,1,3‐Trisubstituted Naphtho[2,3‐ c ]pyran‐5,10‐dione Derivatives as Potential Redox Switches
Author(s) -
Shie TienLan,
Lin ChiHui,
Lin ShihLun,
Yang DingYah
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700426
Subject(s) - chemistry , hydroquinone , sodium borohydride , pyran , quinone , redox , fluorescence , methanol , quantum yield , yield (engineering) , orange (colour) , photochemistry , medicinal chemistry , organic chemistry , catalysis , physics , materials science , food science , quantum mechanics , metallurgy
Five 1,1,3‐trisubstituted naphtho[2,3‐ c ]pyran‐5,10‐dione derivatives were designed and synthesized in five steps from 2‐acetyl‐1,3‐indandione. Prepared quinones 6a – e instantly changed from either red or blue to yellow or orange red, when treated with sodium borohydride in methanol. The resulting reduced hydroquinones 9a – e reverted to their original colors within a few minutes after the reducing agent was consumed or removed. Whereas no fluorescence of blue quinone 6e was detected prior to reduction, reduced hydroquinone 9e emitted red fluorescence with a quantum yield of 0.07.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)