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Modular synthesis of photodegradable polymers with different sensitive wavelengths as UV/NIR responsive nanocarriers

Li, Lei, Wu, Yuhuan, Du, Fu‐Sheng, Li, Zi‐Chen
Journal of polymer science 2019 v.57 no.3 pp. 334-341
absorption, dyes, emulsions, hydrophobicity, nanocarriers, nanoparticles, photolysis, polymerization, polymers, wavelengths
We report the modular and facile synthesis of three novel polymers able to photodegrade by UV and visible light via the Passerini multicomponent polymerizations of 1,6‐hexanedioic acid and 1,6‐diisocyanohexane with 5‐methoxy‐2‐nitrobenzaldehyde (M2), 4,5‐dimethoxy‐2‐nitrobenzaldehyde (M3) or 7‐(N,N‐diethylamino)‐4‐formylcoumarin (M4) respectively. This synthetic strategy takes the advantage of the in situ formation of a photolabile chromophore via the Passerini reaction of an aromatic aldehyde with an acid and an isocyanide, thus it is a versatile approach to regulating the photochemical property of the photolabile chromophores by just changing the aldehyde structure. Importantly, two polymers (P3 and P4) even exhibit NIR degradability due to the two‐photon absorption, and their nanoparticles formulated by the single emulsion method have been used as the NIR‐responsive nanocarriers for hydrophobic dyes. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 334–341