Self‐Assembly of Bowl‐Shaped Naphthalimide‐Annulated Corannulene

ChemistryOpen

卷:9

Prof. Dr. Frank Würthner¹  Dr. Matthias Stolte¹  Rebecca Renner¹ 

[1] Institut für Organische Chemie & Center for Nanosystems Chemistry Universität Würzburg Am Hubland 97074 Würzburg Germany;

关键词: corannulene;    π-π-interactions;    self-assembly;    aggregation;    supramolecular chemistry;   

DOI  :  10.1002/open.201900291

来源: DOAJ

【 摘 要 】

Abstract The self‐assembly of a bowl‐shaped naphthalimide‐annulated corannulene of high solubility has been studied in a variety of solvents by NMR and UV/Vis spectroscopy. Evaluation by the anti‐cooperative K2‐K model revealed the formation of supramolecular dimers of outstanding thermodynamic stability. Further structural proof for the almost exclusive formation of dimers over extended aggregates is demonstrated by atomic force microscopy (AFM) and diffusion ordered spectroscopy (DOSY) measurements as well as by theoretical calculations. Thus, herein we present the first report of a supramolecular dimer of an annulated corannulene derivative in solution and discuss its extraordinarily high thermodynamic stability with association constants up to >106 M−1 in methylcyclohexane, which is comparable to the association constants given for planar phthalocyanine and perylene bisimide dyes.

【 授权许可】

Unknown