Synthesis and photochromism of catechol-containing symmetrical azobenzene compounds.
Synthesis and photochromism of catechol-containing symmetrical azobenzene compounds.
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含儿茶酚对称偶氮苯化合物的合成及光致变色
DOI：
10.1098/rsos.211894
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发表时间：
2022-06
影响因子：
3.5
通讯作者：
中科院分区：
文献类型：
--
作者：
合成了一类新型的含邻苯二酚基团的对称偶氮苯衍生物（1d-4d），其结构经质谱和核磁共振谱确证。这些化合物在紫外光照射下，在溶液中能迅速达到光稳定态，且其光致变色具有良好的可逆性。偶氮苯生色团上的取代基及其位置对化合物的最大吸收和光致变色性能有明显的影响。邻位上的给电子基团对π-π* 带的红移有贡献。与多巴胺分子和偶氮苯环键合的磺酰胺基团引起顺式异构体的可忽略的n-π* 跃迁，导致在UV照射下的光漂白。其中，4d的邻甲氧基取代基给电子能力最强，平面性较低，在相同强度的紫外光照射下，其吸光度下降幅度更大，顺反转化率可达63%。此外，由于邻苯二酚基团的存在，4d对底物表现出较好的亲和性和粘附性，在底物表面，经紫外光照射后可观察到微弱的颜色变化，但可逆性比溶液中差。
Symmetrical azobenzene derivatives with two catechol groups, 1d–4d, were synthesized as kinds of novel compounds, and the structures were confirmed using mass spectrometry and nuclear magnetic resonance spectroscopy. These compounds could attain photostationary state rapidly in solution upon UV irradiation, and their photochromism had good reversibility. Substituents and their positions on azobenzene chromophore had obvious influence on the maximum absorption and photochromic performances of these as-synthesized compounds. Electron-donating group on ortho positions could contribute to the redshift π–π* band. The sulfonamide group that is bonded to dopamine molecules and azobenzene rings caused a negligible n–π* transition of cis isomer, resulting in photobleaching upon UV irradiation. Among the four compounds, 4d had the strongest electron-donating ortho-methoxy substituents and lower planarity; thus its absorption could decrease more significantly upon UV irradiation of the same intensity, and its cis-to-trans conversion could be up to 63%. Furthermore, owing to the presence of catechol groups, 4d showed an effective affinity and adhesion to substrate, and on the surface of substrate, a weak colour change could be observed upon UV irradiation, but the reversibility was poorer than that in solution.
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影响因子：
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