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CC BY-NC-ND 4.0 · Organic Materials 2021; 03(02): 353-361
DOI: 10.1055/a-1503-5912
Focus Issue: Supramolecular Optoelectronic Materials
Original Article

Aqueous Self-Assembly of Peptide–Diketopyrrolopyrrole Conjugates with Variation of N-Alkyl Side Chain and π-Core Lengths

Sayak Subhra Panda 
a   Department of Chemistry, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218, United States
,
John D. Tovar 
a   Department of Chemistry, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218, United States
b   Department of Materials Science and Engineering, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218, United States
› Author Affiliations Funding Information This research is based upon work supported by the National Science Foundation's Designing Materials to Revolutionize and Engineer our Future (DMREF) program (Grant Nos. DMR-1728947).
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Abstract

Peptidic sequences when conjugated to π-electronic groups form self-assembled networks of π-electron pathways. These materials hold promise for bio-interfacing charge transporting applications because of their aqueous processability and compatibility. In this work, we incorporated diketopyrrolopyrrole (DPP), a well-established π-core for organic electronic applications, within the peptidic sequence. We embedded different numbers of thiophene rings (2 and 3) on both sides of the DPP to alter the length of the π-cores. We also varied the length of the N-alkyl side chains (methyl, butyl, hexyl) attached to the DPP core. These variations allowed us to explicitly study the effect of π-core and N-alkyl side-chain length on photophysical properties and morphology of the resulting nanomaterials. All of these molecules formed H-type aggregates in the assembled state. Longer π-cores have relatively red-shifted absorption maxima, whereas the N-alkyl variation did not present significant photophysical changes.

Key words

peptide-π conjugates - diketopyrrolopyrroles - aqueous self-assembly - side-chain engineering

Supporting Information

Supporting Information for this article is available online at https://doi.org/10.1055/a-1503-5912.


Supporting Information



Publication History

Received: 31 March 2021

Accepted: 30 April 2021

Accepted Manuscript online:
08 May 2021

Article published online:
24 June 2021

© 2021. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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