Heteroatom-Promoted Polyhexagonal Saddle-Shaped Molecular Structures and their Supramolecular Coassembly with C60

Thilagar, P and Nandi, RP and Ghosh, S (2024) Heteroatom-Promoted Polyhexagonal Saddle-Shaped Molecular Structures and their Supramolecular Coassembly with C60. In: Chemistry - A European Journal .

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Abstract

Molecules with curved architecture can exhibit unique optoelectronic properties due to the concave-convex �-surface. However, synthesizing negatively curved saddle-shaped aromatic systems has been challenging due to the internal structural strain. Herein, we report the facile synthesis of two polyhexagonal molecular systems, 1 and 2, with saddle shape geometry by judiciously varying the aromatic moiety, avoiding the harsh synthetic methods as that of heptagonal aromatic saddle systems. The unique geometry preferences of B, N, and S furnish suitable curvature to the molecules, featuring saddle shape. The saddle geometry also enables them to interact with fullerene C60, and the supramolecular interactions of fullerene C60 with 1 and 2 modify their optoelectronic properties. Crystal structure analysis reveals that 1, with a small �-surface, forms a double columnar array of fullerenes in the solid state. In contrast, 2 with a large �-surface produces a supramolecular capsule entrapping two discrete fullerenes. The intermolecular interactions between B, N, S, and the aryl-� surface of the host and C60 guest are the stabilizing factors for creating these supramolecular structures. Comprehensive computational, optical, and Raman spectroscopic studies establish the charge transfer interactions between B�N doped heterocycle host and fullerene C60 guest. © 2024 Wiley-VCH GmbH.

Item Type:	Journal Article
Publication:	Chemistry - A European Journal
Publisher:	John Wiley and Sons Inc
Additional Information:	The copyright for this article belongs to John Wiley and Sons Inc.
Keywords:	Aromatic compounds; Aromatization; Boron; Charge transfer; Crystal structure; Geometry; Molecules; Spectroscopic analysis; Supramolecular chemistry, Aromatic system; C 60; Curved saddles; Fullerene (C 60); Heteroatoms; Heterocycles; Optoelectronics property; Polyaromatics; Structural strain; Supramolecules, Fullerenes
Department/Centre:	Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited:	03 Jun 2024 07:25
Last Modified:	03 Jun 2024 07:25
URI:	https://eprints.iisc.ac.in/id/eprint/85132

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