Poly( O ‐Propargyl‐ N ‐Amino Carbamate), a Reactive Polymer to Underpin Biomedical Applications of Poly(acetylene)s
Year: 2025
Type: article
Abstract: ABSTRACT Synthetic polymers are widely used in biomedical applications, yet most lack defined secondary structures common in nature, such as helices or β‐sheets. In particular, dynamic helical polymers such as poly(acetylene)s have been rarely explored in this field. Here, we report the preparation of a new reactive poly(acetylene), poly( O ‐propargyl‐ N ‐amino carbamate) ( P1 ), as a platform for the preparation of functional poly(acetylene)s in water. P1 was prepared from readily available starting materials through Rh‐catalyzed polymerization and acid‐mediated deprotection. 1 H‐NMR indicated that the formed polymer had a high content of cis double bonds, while UV–vis and DSC suggested a predominant cis ‐ cisoid conformation. This conformation was also observed via CD for chiral derivatives of Boc‐protected P1 , while a partially deprotected chiral derivative of P1 could be adopting multiple conformations in solution, including cis ‐ transoid and cis ‐ cisoid conformations. P1 was functionalized under aqueous conditions with a small set of aldehydes, including cationic, aliphatic, and aromatic derivatives, as well as a small set of carbohydrates. Finally, we demonstrate that P1 , and a guanidinium derivative P1‐ mod ‐4 , were well tolerated by cells, highlighting the potential of this polymer to underpin the development of biomedical applications of poly(acetylene)s.
Institutions: University of Birmingham, Universidade da Coruña
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,550
Funders: “la Caixa” Foundation, Ministerio de Ciencia, Innovación y Universidades, Leverhulme Trust, European Commission, Ministerio de Educación, Cultura y Deporte, Ministerio de Ciencia e Innovación, Xunta de Galicia, Engineering and Physical Sciences Research Council, Agencia Estatal de Investigación, HORIZON EUROPE European Innovation Council
Awards: G1541474743, G1743801114, G2206881521, G2262748287, G2763696297, G3480869486, G3681454997, G4042783231, G425668148, G434337789, G4442677895, G4462967385, G4526231891, G47840581, EPSRC Centre for Doctoral Training in Physical Sciences for Health (Sci-Phy-4-Health), G5260651846, G5404935707, G5635532810, G586857820, G6200043914, G6258374248, G679164369, G6904152975, G7084143925, G7434936867, G7863371703, G8008785700, G8497050386, Identifying Chemical Cues in the Polymer-Mediated Engineering of Microorganisms
OpenAlex ID: W4415550939