Journal
MACROMOLECULES
Volume 47, Issue 9, Pages 2974-2983Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ma500454f
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Funding
- National Heart Lung and Blood Institute of the National Institutes of Health as a Program of Excellence in Nanotechnology [HHSN268601000046C]
- National Science Foundation [CHE-1057441]
- Welch Foundation through the W. T. Doherty-Welch Chair in Chemistry [A-0001]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1057441] Funding Source: National Science Foundation
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Ferulic acid (FA), a bio-based resource found in fruits and vegetables, was coupled with a hydroxyl-amino acid to generate a new class of monomers to afford poly(carbonate-amide)s with potential to degrade into natural products. L-Serine was first selected as the hydroxyl-amino partner for FA, from which the activated p-nitrophenyl carbonate monomer was synthesized. Unfortunately, polymerizations were unsuccessful, and the elimination product was systematically obtained. To avoid elimination, we revised our strategy and used L-tyrosine ethyl ester, which lacks an acidic proton on the alpha position of the ethyl ester. Four new monomers were synthesized and converted into the corresponding poly(carbonate-amide)s with specific regioselectivities. The polymers were fully characterized through thermal and spectroscopic analyses. Preliminary fluorescent studies revealed interesting photophysical properties for the monomers and their corresponding poly(carbonate-amide)s, beyond the fluorescence characteristics of L-tyrosine and FA, making these materials potentially viable for sensing and/or imaging applications, in addition to their attractiveness as engineering materials derived from renewable resources.
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