邻苯二甲酸乙基苯胺取代亚酞菁的合成、理化性质及理论计算

IF 0.9 4区 化学 Q4 CHEMISTRY, MULTIDISCIPLINARY Journal of Porphyrins and Phthalocyanines Pub Date : 2023-09-22 DOI:10.1142/s1088424623501201
Oscar Fernandez-Vera, Yifan Bo, Yusen Luo, Jorge Labella, Dirk M. Guldi, Tomas Torres, Giovanni Bottari
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引用次数: 0

摘要

我们在此报道了一种新型的[公式:见文]-亚酞菁(SubPc)基电子给受体缀合物(1)的合成,其中大环在其外围位置被三个苯基-乙基-[公式:见文],[公式:见文]-二甲苯胺基团功能化。后一部分,除了赋予增加稳定性和溶解性的结果体系,大大拓宽其吸收能力。深入的光谱学、光谱学和电化学分析以及对1进行的理论计算表明,大环与正交排列的蒽基-乙基-[公式:见文]、[公式:见文]-二甲苯胺部分之间存在适度的基态分子内相互作用。有趣的是,这种电子通信在激发态中显著增加,这一过程强烈依赖于溶剂的极性。一方面,在甲苯中,在光激发下,观察到一个[公式:见文](子pc)态的形成,在失活到基态之前衰变成一个[公式:见文](子pc)流形。另一方面,增加溶剂对四氢呋喃和苯腈的极性,显著地改变了光激发态的命运。在这种新的情况下,[公式:见文](SubPc)状态,直接形成550 nm光刺激或[公式:见文](anthryl-乙基苯胺)敏化在405 nm激发,转变为电荷转移(SubPc)[公式:见文]-anthryl-乙基苯胺[公式:见文]状态,进一步演变成完全电荷分离(SubPc)[公式:见文]-anthryl-乙基苯胺[公式:见文]物种失活性到基态。
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Synthesis, physicochemical properties and theoretical calculations of a subphthalocyanine peripherally substituted by multiple anthryl-ethynyl-aniline moieties
We report here the synthesis of a novel [Formula: see text]-subphthalocyanine (SubPc)-based electron donor-acceptor conjugate (1) in which the macrocycle has been functionalized at its peripheral positions with three anthryl-ethynyl-[Formula: see text],[Formula: see text]-dimethylaniline groups. The latter moiety, besides conferring increased stability and solubility to the resulting system, substantially broadens its absorption capability. In-depth spectroscopic, spectrometric, and electrochemical analyses as well as theoretical calculations carried out on 1 suggest a moderate ground state intramolecular interaction between the macrocycle and the orthogonally-arranged anthryl-ethynyl-[Formula: see text],[Formula: see text]-dimethylaniline moieties. Interestingly, such electronic communication significantly increases in the excited state in a process strongly depending on the polarity of the solvent. On the one hand, in toluene, upon photoexcitation of the anthryl-ethynyl-aniline, the formation of a [Formula: see text](SubPc) state is observed which decays into a [Formula: see text](SubPc) manifold before deactivating to the ground state. On the other hand, increasing the polarity of the solvent to tetrahydrofuran and benzonitrile, significantly modifies the fate of the photoexcited state. In this new scenario, the [Formula: see text](SubPc) state, formed directly upon 550 nm light stimulation or by [Formula: see text](anthryl-ethynyl-aniline) sensitization upon 405 nm excitation, transforms into a charge transfer (SubPc)[Formula: see text]-anthryl-ethynyl-aniline[Formula: see text] state which further evolves into a fully charge-separated (SubPc)[Formula: see text]-anthryl-ethynyl-aniline[Formula: see text] species before deactivating to the ground state.
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来源期刊
CiteScore
2.10
自引率
20.00%
发文量
62
审稿时长
1 months
期刊介绍: The Journal of Porphyrins and Phthalocyanines (JPP) covers research in the chemistry, physics, biology and technology of porphyrins, phthalocyanines and related macrocycles. Research papers, review articles and short communications deal with the synthesis, spectroscopy, processing and applications of these compounds.
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