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Chiral Supramolecular Assemblies from an Achiral Naphthalene Diimide Bearing a Urea Moiety
Author(s) -
Shaikh Dada B.,
Bhosale Rajesh S.,
La Duong Duc,
Al Kobaisi Mohammad,
Bhosale Sidhanath V.,
Bhosale Sheshanath V.
Publication year - 2018
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201801115
Subject(s) - supramolecular chemistry , moiety , circular dichroism , crystallography , supramolecular assembly , molecule , perylene , chirality (physics) , supramolecular chirality , chemistry , diimide , materials science , stereochemistry , photochemistry , crystal structure , organic chemistry , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , quark
The ordering of organic molecules in a supramolecular self‐assembly determines their physical, chemical, and photonic properties. Here, we report the aggregation of two achiral naphthalene diimides (NDIs), in which phenyl moieties are linked to the NDI core via a urea subunit, leading to chiral supramolecular assemblies in THF/methylcyclohexane. Circular dichroism spectroscopic analysis of twisted ribbons deposited from solutions indicated a mixture of left‐ and right‐handed nanostructures for one NDI, whereas only left‐handed structures were observed for the other one. Furthermore, this study also shows the effect of large atoms such as iodine on the self‐assembly process, which governs and controls the helicity of the produced microstructures. The supramolecular assemblies were characterized by UV/Vis, fluorescence emission, CD, SEM, and XRD techniques.