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- Title
Supramolecular Chiral Helical Ribbons of Tetraphenylethylene‐Appended Naphthalenediimide Controlled by Solvent and Induced by l‐ and d‐Alanine Spacers.
- Authors
Goskulwad, Santosh P.; Kobaisi, Mohammad Al; La, Duong Duc; Bhosale, Rajesh S.; Ratanlal, Malavath; Bhosale, Sidhanath V.; Bhosale, Sheshanath V.
- Abstract
Naphthalenediimide‐tetraphenylethylene conjugates with an alanine spacer (coded as: NDI‐(Ala‐TPE)2) were synthesized to study the influence of the chirality of the amino acid spacer on its self‐assemblies. Here we particularly show that NDI‐Ala‐TPE bearing l‐alanine gives left‐handed (M‐type) helical superstructure, while d‐alanine produces right‐handed (P‐type) helical ribbons in THF:H2O at 40:60 % v/v ratio. However, particular aggregates were observed at 20:80 % v/v ratio. Circular dichroism was used to characterise the induction of chirality and the handedness of the helical superstructures, and the microstructure of the self‐assembled materials was visualised using scanning electron microscopy while DLS analysis confirmed the formation of particular aggregates in solution. Giving a hand: The formation of controlled supramolecular structures of naphthalenediimide (NDI) bearing two tetraphenylethylene (TPE) units at the imide position in THF/water and chirality induction by l‐ and d‐alanine are described. In particular, NDI‐Ala‐TPE bearing l‐alanine gives a left‐handed helical superstructure, while d‐alanine produces right‐handed helical ribbons in THF:H2O at 40:60 % v/v ratio. However, particular aggregates were observed at 20:80 % v/v ratio.
- Subjects
TETRAPHENYLETHYLENE; SUPRAMOLECULAR chemistry; CRYSTAL structure; CHIRALITY; ALANINE; DICHROISM
- Publication
Chemistry - An Asian Journal, 2018, Vol 13, Issue 24, p3947
- ISSN
1861-4728
- Publication type
Article
- DOI
10.1002/asia.201801421