Issue 8, 2021

Functionalized naphthalenediimide based supramolecular charge-transfer complexes via self-assembly and their photophysical properties

Abstract

We report here the design and syntheses of a naphthalenediimide (NDI)-N functionalized organic fluorophore, 1, and its supramolecular CT complexes [(1·2H)2+·(PA)2] (2) and [(1·2H)2+·(3,5-DNSA)2] (3), self-assembled from 1 as an electron acceptor (A) and picric acid (PA) or 3,5-dinitrosalicylic acid (3,5-DNSA) as a donor (D), with a very large Stokes shift (>170 nm) and significant fluorescence lifetime (∼1.55 ns). NDI is functionalized with phenylpyridyl units (chromophore) to extend the π-conjugation and thus provide a suitable platform for strong C–H---π and π⋯π stacking interactions, which are the prime requirements for any compound to be used as a fluorescent probe. The organic fluorophore, 1, and its supramolecular CT complexes 2 and 3 exhibit decent electronic properties as suggested by DFT, cyclic voltammetry, and fluorescence studies. Moreover, compounds 1–3 were also exploited as fluorescent probes for cell imaging under normal cell isolation and with time-bound exposure.

Graphical abstract: Functionalized naphthalenediimide based supramolecular charge-transfer complexes via self-assembly and their photophysical properties

Supplementary files

Article information

Article type
Paper
Submitted
25 Nov 2020
Accepted
06 Jan 2021
First published
07 Jan 2021

CrystEngComm, 2021,23, 1859-1869

Functionalized naphthalenediimide based supramolecular charge-transfer complexes via self-assembly and their photophysical properties

P. Rani, A. Husain, A. Shukla, N. Singla, A. K. Srivastava, G. Kumar, K. K. Bhasin and G. Kumar, CrystEngComm, 2021, 23, 1859 DOI: 10.1039/D0CE01719A

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