Synthesis, characterisation and chiroptical properties of ‘click’able polyisocyanopeptides

Cysteine‐Containing Polyisocyanides as Versatile Nanoplatforms for Chromophoric and Bioscaffolding

“…1 H and 13 C NMR spectra were recorded on a Bruker AC-300 MHz instrument operating at 300 and 75 MHz, respectively. FTIR spectra were recorded on a ThermoMattson IR300 spectrometer equipped with a Harrick ATR unit and the compounds were measured as a solid or an oil.…”

“…[13] Water-soluble dye-containing polymers, which are promising as novel biomarker materials, have been obtained from these "click"able polyisocyanides. [14] As part of this program, we also became interested in introducing thiol functionalities into the lateral chains to extend the postmodification strategy and to increase the applications of these well-defined macromolecules.…”

Click Chemistry: A Powerful Tool to Create Polymer‐Based Macromolecular Chimeras

“…[56] (C) Synthesis of polyester-graft-GRGDS as reported by Emrick and coworkers [57] using CuSO 4 /Na ascorbate click catalytic system at 100 8C. (D) Click functionalization of an alkyne-functionalized rigid rod poly(isocyanopeptide) scaffold as reported by Cornelissen and coworkers [59] using the CuBr/pentamethylene diethyltriamine (PMDETA) complex as catalyst.…”

“…Indeed, the subsequent copper mediated clicking of azide-terminated PEGs and oligopeptides proceeded successfully under click chemistry conditions without appreciable polyester degradation and led to the desired amphiphilic and biotailored graft peptidic copolymers that are expected to be useful in several arenas including that of polymer-based delivery applications ( Figure 2C). Following their work on the synthesis of polyisocyanopeptides, [58] Cornelissen and coworkers [59] recently reported on the synthesis of alkyne-functionalized rigid rod polyisocyanopeptides containing acetylene groups on the side arms as scaffolds that can be multifunctionalized by the copper-catalyzed click reaction as it was demonstrated using aliphatic tails functionalized with azide moieties such as dodecyl azide ( Figure 2D). The creation of combinatorial libraries of assembled and scaffolded peptides is undoubtedly one of the emerging areas in biomedicine and biotechnology.…”

Helix Formation of Poly(phenylacetylene)s Bearing Azide Groups through Click Polymer Reaction with Optically Active Acetylenes

“…However, the successful examples where the click reaction was employed for preparing optically active helical polymers are still scarce [5][6][7][8][9][10] despite the attractive applications to chiral materials. [11][12][13][14][15][16][17][18] Recently, we reported a novel approach to the synthesis of diverse optically active polymers using the click reaction.…”