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Synthesis and Emergent Photophysical Properties of Diketopyrrolopyrrole-Based Supramolecular Self-Assembly

Maity, N and Majumder, K and Patel, AK and Swain, D and Suryaprakash, N and Patil, S (2022) Synthesis and Emergent Photophysical Properties of Diketopyrrolopyrrole-Based Supramolecular Self-Assembly. In: ACS Omega, 7 (27). pp. 23179-23188.

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Official URL: https://doi.org/10.1021/acsomega.2c01091


Diketopyrrolopyrrole (DPP)-based molecular semiconductors exhibit intriguing optical and charge transport properties. Herein, we rationally design a series of electronically identical but structurally distinct Hamilton receptor (HR)-based supramolecular assembly of DPP. The HR endows supramolecular assemblies via hydrogen bonding with enhanced structural ordering and excitonic couplings. The mechanism of supramolecular self-assembly was probed by diffusion ordered spectroscopy (DOSY) nuclear magnetic resonance (NMR) and solid-state IR spectroscopy studies. We investigated the morphology of self-assembly, photophysical and electrochemical properties and compared them with the identical DPP molecular structures without HRs. The microstructure of self-assembly was probed with atomic force microscopy in thin films. Subsequently, the influence of solid-state packing was studied by single-crystal X-ray diffraction. The single-crystal structure of HR-TDPP-C20 reveals slipped stack arrangements between the two neighboring chromophores with π-πstacking distance and slip angle of 3.55 Å and 35.4°, respectively. Notably, the slight torsional angle of 1° between thiophene and lactam rings and small π-πstacking distance suggest a significant intermolecular coupling between thiophene (D) and lactam (A) rings. This intramolecular coupling between two π-πchromophore stacks manifests in their optical properties. In this manuscript, we report rational design and synthesis of supramolecular self-assembly of DPP with a collection of compelling structural and optical properties.

Item Type: Journal Article
Publication: ACS Omega
Publisher: American Chemical Society
Additional Information: The copyright for this article belongs to the Authors.
Department/Centre: Division of Biological Sciences > Molecular Biophysics Unit
Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited: 10 Aug 2022 05:56
Last Modified: 10 Aug 2022 05:56
URI: https://eprints.iisc.ac.in/id/eprint/75788

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