Issue 3, 2023

Angularly fused diaza-dinaphthopyrenes: regio-selective synthesis, crystal structures and isomer-dependent mechanochromic fluorescent properties

Abstract

We report a one-pot synthesis of a series of unprecedented angular-fused diaza-dinaphthopyrene isomers (1,8-DNPy and 1,6-DNPy) in high yields, which are enabled by regio-selective Bischler–Napieralski cyclization to fuse two quinolone rings either on the same or opposite faces of a pyrene core. Benefiting from the high reactivity of the 1- and 8-positions of the pyrene ring, steric effect from substitution and remarkably different dipole moments, high ring closure selectivity for the 1,8-form vs. the 1,6-form up to 6 : 1 is achieved with ease of separation. With differentiated molecular symmetry, conformation, intermolecular interactions and aromaticity, the two kinds of regio-isomers exhibit distinct single-crystal structures and optoelectronic properties. Impressively, isomer-dependent mechanochromic fluorescent properties of these 2D-azaacenes are identified, which are unique in their turn-on fluorescence feature and contrasting spectral shifts. These findings allow facile and modular access to regio-specific 2D-N-heteroarenes, which provide a way to create innovative optical sensors with improved sensitivity and fruitful fluorescent properties.

Graphical abstract: Angularly fused diaza-dinaphthopyrenes: regio-selective synthesis, crystal structures and isomer-dependent mechanochromic fluorescent properties

Supplementary files

Article information

Article type
Edge Article
Submitted
10 Okt. 2022
Accepted
28 Nov. 2022
First published
03 Dec. 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2023,14, 668-674

Angularly fused diaza-dinaphthopyrenes: regio-selective synthesis, crystal structures and isomer-dependent mechanochromic fluorescent properties

Y. Kou, G. Li, Y. Han, M. Li, T. Wang, Z. Qu and Y. Chen, Chem. Sci., 2023, 14, 668 DOI: 10.1039/D2SC05608A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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