Open AccessSelf‐Assembly of Bowl‐Shaped Naphthalimide‐Annulated Corannulene
Author(s) -
Renner Rebecca,
Stolte Matthias,
Würthner Frank
Publication year - 2020
Publication title -
chemistryopen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.644
H-Index - 29
ISSN - 2191-1363
DOI - 10.1002/open.201900291
Subject(s) - corannulene , supramolecular chemistry , chemistry , perylene , dimer , methylcyclohexane , phthalocyanine , self assembly , solvatochromism , spectroscopy , supramolecular polymers , derivative (finance) , fullerene , crystallography , organic chemistry , toluene , molecule , crystal structure , physics , quantum mechanics , financial economics , economics
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 K 2 ‐ 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 >10 6 M −1 in methylcyclohexane, which is comparable to the association constants given for planar phthalocyanine and perylene bisimide dyes.