Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 8, Pages 3929-3939Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b00244
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Funding
- Spanish Ministerio de Ciencia e Innovacion (MICINN)/Fondos Europeos para el Desarrollo Regional (FEDER) [CTQ2011-24800, CTQ2012-36966]
- Spanish MEC
- National Science Foundation, USA [CHE 1229339, CHE1429086]
- [CCG2013/EXP-089]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1229339] Funding Source: National Science Foundation
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1429086] Funding Source: National Science Foundation
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A new family of molecular photoswitches based on arylidenehydantoins is described together with their synthesis and photochemical and photophysical studies. A series of hydantoin derivatives have been prepared as single isomers using simple and versatile chemistry in good yields. Our studies show that the photostationary states of these compounds can be easily controlled by means of external factors, such as the light source or filters. Moreover, the detailed investigations proved that these switches are efficient (i.e., they make efficient use of the light energy, are high fatigue resistant, and are very photostable). In some cases, the switches can be completely turned on/off, a desirable feature for specific applications. A series of theoretical calculations have also been carried out to understand the photoisomerization mechanism at the molecular level.
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