Schulze Erik J, Ritterhoff Christian L, Franz Evanie, Tavlui Olha, Brummel Olaf, Meyer Bernd, Hirsch Andreas
Department of Chemistry & Pharmacy, Chair of Organic Chemistry II, Friedrich-Alexander-Universität Erlangen-Nürnberg, Nikolaus-Fiebiger-Straße 10, 91058, Erlangen, Germany.
Interdisciplinary Center for Molecular Materials (ICMM) and Computer Chemistry Center (CCC), Friedrich-Alexander-Universität Erlangen-Nürnberg, Nägelsbachstraße 25, 91052, Erlangen, Germany.
Chemistry. 2024 Feb 21;30(11):e202303515. doi: 10.1002/chem.202303515. Epub 2024 Jan 10.
We report on the synthesis and characterization of a family of three water-soluble bola-amphiphilic zinc-porphyrin-perylenebisimide triads containing oligo carboxylic-acid capped Newkome dendrons in the periphery. Variations of the perylenebisimide (PBI) core geometry and dendron size (G1 and G2 dendrons with 3- and 9-carboxylic acid groups respectively) allow for tuning the supramolecular aggregation behavior with respect to variation of the molecular architecture. The triads show good solubility in basic aqueous media and aggregation to supramolecular assemblies. Theoretical investigations at the DFT level of theory accompanied by electrochemical measurements unravel the geometric and electronic structure of the amphiphiles. UV/Vis and fluorescence titrations with varying amounts of THF demonstrate disaggregation.
我们报道了一系列三种水溶性bola-两亲性锌卟啉-苝二酰亚胺三联体的合成与表征，其外围含有寡聚羧酸封端的纽科姆树枝状分子。苝二酰亚胺（PBI）核心几何结构和树枝状分子大小（分别为带有3个和9个羧酸基团的G1和G2树枝状分子）的变化使得能够根据分子结构的变化调节超分子聚集行为。这些三联体在碱性水性介质中显示出良好的溶解性，并聚集形成超分子组装体。在密度泛函理论（DFT）水平上的理论研究以及电化学测量揭示了两亲分子的几何和电子结构。用不同量的四氢呋喃（THF）进行紫外/可见和荧光滴定表明发生了解聚。
