Tröger's base-Amino-1,8-Naphthalimides - An Emerging Supramolecular Scaffolds for Self-Assembly Structures and Materials Design

Abstract

Supramolecular self-assembly chemistry provides a fascinating platform for developing functional structures and materials that can have applications in various fields [1]. Self-assembly is the spontaneous association of components into well-defined ensembles based on the information embedded in the components [2]. In the past few years, we have been interested in the rational design and synthesis of amino-1,8-naphthalimide-derived Tröger’s bases (TBNaps) fluorophores and employ them as bifunctional supramolecular scaffolds to generate hierarchical functional structures and novel materials for applications within the material and medicinal chemistry fields [2-7]. TBNaps are fascinating chiral scaffolds, comprising a methano-1,5-diazocine ring fused with two 1,8-naphthalimide molecules placed orthogonal to each other giving rise to a unique V-shaped structure possessing a hydrophobic cavity [3]. The ease of synthesis, its unique cleft-shaped structure, and its interesting photophysics have made TBNaps an attractive scaffold for use in host-guest systems and numerous supramolecular constructs [4-8]. We have developed several interesting structures, materials, and polymers made from TBNaps and demonstrated their applications. For instance, a novel Tröger’s base p-cymene–Ru(II)–curcumin organometallic conjugate was used as a theranostic agent against cervical cancer cells [6-8]. Recently, we have developed a TBNaps functionalized Triazine covalent organic polymer for ‘turn-on’ fluorescent sensing of volatile organic pollutants [9-14]. In this talk, I will discuss in detail the recent advancements in supramolecular self-assembly formations of novel structures and functional materials made from TBNaps.