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Biobased, Degradable, and Conjugated Poly(Azomethine)s

Cite this: J. Am. Chem. Soc. 2023, 145, 6, 3606–3614
Publication Date (Web):February 7, 2023
https://doi.org/10.1021/jacs.2c12668
Copyright © 2023 American Chemical Society

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    Abstract

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    Carotenoids are a class of biobased conjugated molecules that bear a resemblance to the substructure of polyacetylene, a well-known conductive but insoluble polymer. Solubility is an important physical attribute for processing materials using different techniques. To impart solubility in polymers, alkyl side chains are often included in the molecular design. While these design strategies are well explored in conjugated systems, they have not been implemented with carotenoids as a building block in polymers. Here, we show a series of carotenoid-based polymers with varying side chain lengths to tune solubility. Using carotenoid and p-phenylenediamine-based monomers, degradable and biobased poly(azomethine)s were synthesized via imine polycondensation. Maximum solubilities corresponding to the varying alkyl chain lengths were quantitatively determined by ultraviolet–visible (UV–vis) absorption spectroscopy. Since carotenoids are biobased with known degradation products, the effect of acidic and artificial sunlight-promoted degradation was systematically investigated using UV–vis spectroscopy, 1H nuclear magnetic resonance (NMR) spectroscopy, infrared (IR) spectroscopy, gel permeation chromatography (GPC), and high-resolution mass spectroscopy (HRMS). Our polymer system was found to have two modes of on-demand degradation, with acid hydrolysis accelerating the rate of polymer degradation and artificial sunlight generating additional degradation products. This work highlights carotenoid monomers as viable candidates in the design of biobased, degradable, and conjugated polymers.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/jacs.2c12668.

    • Detailed synthetic procedure, IR, NMR, DOSY, GPC, UV–vis, and HRMS data (PDF)

    • p(CP-hexyl)degradation via acid hydrolysis (5x video speed, addition of 50 μL of 1.5 M HCl each time, polymer concentration 0.0126 mg/mL in THF) (MP4)

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    Cited By

    This article is cited by 2 publications.

    1. Max Wamsley, Shengli Zou, Dongmao Zhang. Advancing Evidence-Based Data Interpretation in UV–Vis and Fluorescence Analysis for Nanomaterials: An Analytical Chemistry Perspective. Analytical Chemistry 2023, 95 (48) , 17426-17437. https://doi.org/10.1021/acs.analchem.3c03490
    2. Nathan Sung Yuan Hsu, Angela Lin, Azalea Uva, Shine Han Huang, Helen Tran. Direct Arylation Polymerization of Degradable Imine-Based Conjugated Polymers. Macromolecules 2023, 56 (21) , 8947-8955. https://doi.org/10.1021/acs.macromol.3c01986

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