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Molecular self-assembly of porphyrin and BODIPY chromophores connected with diphenylalanine moieties
Journal of Porphyrins and Phthalocyanines ( IF 1.5 ) Pub Date : 2020-05-20 , DOI: 10.1142/s1088424619501864
Emmanouil Nikoloudakis 1 , Emmanouil Orphanos 1 , Eleni Agapaki 1 , Vasilis Nikolaou 1 , Asterios Charisiadis 1 , Georgios Charalambidis 1 , Anna Mitraki 2 , Athanassios G. Coutsolelos 1
Affiliation  

In this study, a series of diphenylalanine tetra-substituted porphyrin derivatives were synthesized and their self-assembly ability was extensively studied. Apart from investigating the impact of incorporating many peptide moieties onto a porphyrin molecule; another perspective was investigated as well, namely the connection of two different chromophore entities (porphyrin and BODIPY) onto the same diphenylalanine molecule. Interestingly, various supra-molecular nanostructures were observed depending on the solvent mixture as well as the protecting group of the peptides, namely spheres, plaques and fibrils. The obtained self-assemblies were studied via UV-vis absorption and emission spectroscopies. Mainly red shifting was observed, indicating the formation of J-aggregates in the self-assembled state. However, in one case a blue shifted UV-vis spectrum was obtained suggesting the formation of H-type aggregates. Concerning the porphyrin-diphenylalanine-BODIPY derivative, additional fluorescence studies were performed in order to examine a possible interaction between the two chromophores in the excited state. Indeed, the emission measurements indicated that upon photo-excitation of the BODIPY entity, a very efficient energy or electron transfer process takes place from the BODIPY molecule to the porphyrin macrocycle.

中文翻译:

卟啉和与二苯丙氨酸部分连接的 BODIPY 发色团的分子自组装

本研究合成了一系列二苯丙氨酸四取代卟啉衍生物,并对其自组装能力进行了深入研究。除了研究将许多肽部分结合到卟啉分子上的影响之外;还研究了另一种观点,即两种不同的发色团实体(卟啉和 BODIPY)连接到相同的二苯丙氨酸分子上。有趣的是,根据溶剂混合物以及肽的保护基团,即球体、斑块和原纤维,观察到各种超分子纳米结构。研究了获得的自组装通过紫外可见吸收和发射光谱。主要观察到红移,表明形成Ĵ-聚集在自组装状态。然而,在一种情况下,获得了蓝移的紫外可见光谱,表明形成了H型聚合。关于卟啉-二苯丙氨酸-BODIPY 衍生物,进行了额外的荧光研究,以检查处于激发状态的两个发色团之间可能存在的相互作用。事实上,发射测量表明,在 BODIPY 实体的光激发下,从 BODIPY 分子到卟啉大环发生了非常有效的能量或电子转移过程。
更新日期:2020-05-20
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