Premium
Alternating Placement of d ‐ and l ‐Alanine Moieties in the Polymer Side‐Chains
Author(s) -
Goswami Krishna Gopal,
Saha Biswajit,
Mete Sourav,
De Priyadarsi
Publication year - 2018
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.201800398
Subject(s) - chemistry , monomer , polymer chemistry , side chain , polymer , alanine , copolymer , polymerization , aqueous solution , protonation , organic chemistry , amino acid , ion , biochemistry
Synthesis of a sequence‐controlled polymer via reversible addition‐fragmentation chain transfer polymerization is reported herein, using an N ‐substituted maleimide monomer bearing tert ‐butyl carbamate (Boc)‐protected l ‐alanine ( M1 ) and Boc‐ d ‐alanine appended styrenic monomer ( M2 ). The monomer sequence distribution along the polymer chain is thoroughly studied by 1 H and 13 C NMR spectroscopy and matrix‐assisted laser desorption/ionization time‐of‐flight mass spectrometry, confirming the alternating placement of l ‐alanine and d ‐alanine throughout the polymer chain. Copolymers display fluorescence properties in various organic solvents. After the deprotection of Boc‐groups, the copolymers show fluorescence activity in water (and also in several organic solvents), and pH‐responsiveness in aqueous medium due to the protonation/deprotonation of the side‐chain ‐NH 2 groups at varying aqueous solution pH. In addition, the presence of different enantiomeric structures of alanine in the side‐chain enables us to investigate the chiroptical properties of the polymers.