Synthesis of diisocyanides with phenolic groups and their polymerization to helically chiral poly(quinoxaline‐2, 3‐diyl)s. Issue 11 (4th March 2015)

• Record Type: Journal Article
• Authors: Scholz, Johannes; Reggelin, Michael
• Is Part Of: Journal of polymer science. Volume 53:Issue 11(2015:Jun.)
• Page Start: 1320
• Page End: 1329
• Publication Date: 2015-03-04
• Subjects: functionalization of polymers -- helically chiral polymers -- heteroatom containing polymers -- poly(quinoxalin‐2, 3‐diyl)s -- supramolecular structures; 547
• DOI: 10.1002/pola.27580
• Languages: English
• ISSNs: 0887-624X

Abstract

ABSTRACT: The development of synthetic routes which lead to five new diisocyanide monomers with one or two phenolic groups is described. Their polymerization behavior is studied with Pd‐ and Ni‐based initiators, as well as under microwave irradiation. The polymerizability is mainly dominated by steric effects as is concluded from experiments using different protecting groups. Chiroptical properties of these new polymers are studied by CD‐spectroscopy. After deprotection, helically chiral poly(quinoxalin‐2, 3‐diyl)s are obtained which display a Brønsted function attached to a stereolabile biaryl axis whose configuration should be influenced by the chiral polymer backbone. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem.2015, 53, 1320–1329 Abstract : The synthesis of new diisocyanide monomers with one or two phenolic groups is described. Their polymerization ability is affected mainly by steric crowding of the diisocyanide functions by adjacent groups. With a chiral Pd‐initiator a helix‐sense selective polymerization is achieved and deprotection is done successfully. The obtained optically active polymers with Brønsted functionalities in each repeating unit are thought as chiral, reusable organocatalysts.