Reversible Photochemical Isomerization of N,N′-Di(t-butoxycarbonyl)indigos
Reversible Photochemical Isomerization of N,N′-Di(t-butoxycarbonyl)indigos
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DOI：
10.1021/jp512346z
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发表时间：
2015-04-16
影响因子：
2.9
通讯作者：
Sariciftci, Niyazi Serdar
中科院分区：
文献类型：
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作者：
Farka, Dominik;Scharber, Markus;Sariciftci, Niyazi Serdar
报道了N，N‘-二(叔丁氧基甲酰基)吲哚(TBOC Indigos)的光物理，发现可逆光化学反式和顺式异构化反应具有很高的量子产率(0.10-0.46)。在500-600 nm波长范围内的吸收导致反式顺式异构化，而蓝光则导致反式顺式-反式过程。和它们的母体Indigos一样，反式BOC Indigos的荧光产额很低(类似于1×10(-3))，而顺式异构体没有可测量的发射。这些化合物是第一批可光异构化的吲哚类染料，其中光化学异构化有效地击败了辐射衰变过程。虽然蓝色染料在有机溶剂中的溶解性通常很差，但tBOC靛蓝在丙酮等常见有机溶剂中的浓度可达8w%。此外，与其他可光异构化的Indigoid不同，tBOC Indigos对质子和电子给体的猝灭不敏感。这些特点，再加上相对较低能量的光子(类似于2 eV)诱导的可逆光异构化的高量子产率，使得tBOC Indigo衍生物在光致变色应用中具有潜在的兴趣，例如光机械驱动材料。
We report on the photophysics of N,N'-di(t-butoxycarbonyl)indigos (tBOC indigos), finding that reversible photochemical trans-cis and cis-trans isomerization reactions proceed with high quantum yields (0.10-0.46). Absorption of wavelengths in the 500-600 nm region induces trans-cis isomerism, while blue light leads to the reverse cis-trans process. Like their parent indigos, trans-BOC indigos have low fluorescence yields (similar to 1 x 10(-3)), while the cis isomers have no measurable emission. These compounds are the first examples of photoisomerizable indigoid dyes in which photochemical isomerism effectively outcompetes radiative decay processes. Though indigo dyes typically have poor solubility in organic solvents, tBOC indigos can be dissolved at concentrations up to 8 w% in common organic solvents like acetone. Furthermore, unlike other photoisomerizable indigoids, tBOC indigos are not sensitive to quenching by proton and electron donors. These features, combined with high quantum yields of reversible photoisomerism induced by relatively low-energy photons (similar to 2 eV), make tBOC indigo derivatives potentially interesting for photochromic applications, such as photomechanically actuated materials.