Fluorescent 4-amino-1,8-naphthalimide Tr?ger's bases (TBNaps) possessing (orthogonal) ‘α-amino acids’, esters and di-peptides and their solvent dependent photophysical properties?

Organic & Biomolecular Chemistry Pub Date: 2021-07-02 DOI: 10.1039/D1OB00973G

Abstract

The synthesis of fifteen luminescent bis-naphthalimide based Tr?ger's bases (TBNaps) derived from 4-amino-1,8-naphthalimide (4-Amino-Nap) precursors is described; these scaffolds possess α-amino acids, esters or di-peptides conjugated at the imide site and show minor fluorescence in aqueous solution while being highly emissive in organic solvents. The investigation shows that these TBNaps possessing ICT excited state properties are capable of generating either positive or negative solvatochromic effects in response to changes in polarity and/or the hydrogen bonding capabilities of the medium.

Graphical abstract: Fluorescent 4-amino-1,8-naphthalimide Tr?ger's bases (TBNaps) possessing (orthogonal) ‘α-amino acids’, esters and di-peptides and their solvent dependent photophysical properties
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