Issue 23, 2022

Harnessing solution and solid-state emissive materials from aliphatic biogenic amine-induced transient assembly and spontaneous disassembly

Abstract

Molecular self-assembly can be described as an appealing approach to uncovering numerous exciting and undesired outcomes, worthily useful in a vast realm of real-world applications. Apart from the elegant synthetic design of organic chromophores, creating a pathway to drive the self-assembly in a solution is always desirable. Inspiringly, this study elucidates how the aliphatic biogenic amines (BAs) influence the transient assembly and disassembly of a pyrene dianhydride (Py-DA)-based scaffold via the nucleophilic reaction. The evolution of the transient assembly via ground-state pre-association and disassembly was established from detailed spectroscopic and microscopic investigations. The driving forces for the stabilization of ground-state aggregate were accessed to be strong H-bonding and π–π interactions between polar pyrene-biogenic amine (Py-BA) conjugates, as unraveled by computational study. HRMS and IR measurements validated the existence of Py-BA conjugates in an open conformation, and NMR analysis also manifested the formation of a mixture of two regioisomers (major >85%) in addition to dimer (minor, <15%) in the solution. The rate of both assembly and disassembly in the solution was affected by the alkyl chain length in the BA skeleton. The reaction-based association–dissociation process eventually assisted in a smooth transition of cyan emission (Py-DA) to yellow (Py-BA excimer) to light blue (Py-BA monomer) through an intermediate white light emission in the solution. The light-blue emissive Py-BA conjugates appeared as yellowish-orange solid-state emitters. Finally, selective Py-BA conjugates were found to be of potential biological significance as they were exclusively localized in the lysosomal compartment of the live cells. Moreover, the stimulated lysosomal membrane-degradation could be visualized through confocal microscopy. This work exemplifies the conversion of a non-polar substrate into water-soluble products via transient assembly and disassembly.

Graphical abstract: Harnessing solution and solid-state emissive materials from aliphatic biogenic amine-induced transient assembly and spontaneous disassembly

Supplementary files

Article information

Article type
Research Article
Submitted
25 محرم 1444
Accepted
30 صفر 1444
First published
30 صفر 1444

Mater. Chem. Front., 2022,6, 3489-3503

Harnessing solution and solid-state emissive materials from aliphatic biogenic amine-induced transient assembly and spontaneous disassembly

R. Roy, A. Pramanik, T. Dutta, V. Sharma, Kovida and A. L. Koner, Mater. Chem. Front., 2022, 6, 3489 DOI: 10.1039/D2QM00861K

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