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Synthesis, electronic structure and NH-tautomerism of novel mono- and dibenzoannelated phthalocyanines
Dyes and Pigments ( IF 4.5 ) Pub Date : 2020-05-21 , DOI: 10.1016/j.dyepig.2020.108564
Alexey V. Yagodin , Alexander G. Martynov , Yulia G. Gorbunova , Aslan Yu Tsivadze

Novel low-symmetry benzoannelated metal-free phthalocyanines of A3B-, ABAB- and AABB-types were synthesized by statistical condensation of phthalonitrile bearing bulky solubilizing groups (fragment A) and new naphthalonitrile with OH-terminated diethylene glycol anchors (fragment B). Comprehensive physical-chemical characterization of the synthesized macrocycles allowed to reveal the electronic effects associated with the extension of π-system. The interpretation of the observed effects was performed by theoretical calculations where simplified TD-DFT approach at CAM-B3LYP/6-31G(d) level was successfully used for the first time to predict excitation energies of Q-band region in UV–Vis spectra of low-symmetry phthalocyanines with errors not exceeding 0.03 eV. Altogether it allowed to identify the spectroscopic signatures of various tautomers including energy-unfavourable forms.



中文翻译:

新型单和二苯甲酰化酞菁的合成,电子结构和NH-互变异构

新型低对称性的A 3苯甲酰化无金属酞菁B-,ABAB-和AABB型是通过带有庞大增溶基团(片段A)和新萘腈与OH封端的二甘醇锚定剂(片段B)的统计缩合合成的。合成的大环化合物的全面物理化学表征可以揭示与π系统扩展相关的电子效应。通过理论计算对观察到的效应进行解释,其中首次成功地使用了CAM-B3LYP / 6-31G(d)级的简化TD-DFT方法来预测UV-Vis光谱中Q波段区域的激发能误差不超过0.03 eV的低对称酞菁。总之,它可以鉴定各种互变异构体的光谱特征,包括不利于能量的形式。

更新日期:2020-06-18
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