Effect of the Diacetylene Position on the Chromatic Properties of Polydiacetylenes from Self-Assembled Peptide Amphiphiles
- 25 May 2010
- journal article
- Published by American Chemical Society (ACS) in Biomacromolecules
- Vol. 11 (6), 1676-1683
- https://doi.org/10.1021/bm100376q
Abstract
Three diacetylene-containing peptide amphiphiles, with exactly the same structure, except for the position of the diacetylene moiety within the hydrophobic tail, were investigated on their assembly behavior, polymerization characteristics, and chromatic properties. After polymerization it was found that the color and, thus, the conjugation length of the polydiacetylenes was dependent both on mobility and on packing of the groups on both sides of the triple bonds. The polydiacetylene with the highest conjugation length and most stable structure was obtained when the diacetylenes were positioned in the middle of the hydrophobic tail. When the diacetylenes were close to the peptide, the mismatch between hydrogen bond and alkyl tail spacing resulted in a decreased conjugation length of the resulting polymer, while when positioned close to the end of the amphiphile the mobility of the terminal alkyl chains hampered the packing of the diacetylenes.Keywords
This publication has 56 references indexed in Scilit:
- Self-Assembly and Polymerization of Diacetylene-Containing Peptide Amphiphiles in Aqueous SolutionBiomacromolecules, 2008
- Peptide Amphiphile Nanofibers with Conjugated Polydiacetylene Backbones in Their CoreJournal of the American Chemical Society, 2008
- The Development of a Generic Bioanalytical Matrix Using PolydiacetylenesAdvanced Functional Materials, 2007
- Antibody-functionalized polydiacetylene coatings on nanoporous membranes for microorganism detectionChemical Communications, 2006
- Kinetic Isotope Effects in the Thermal C2−C6 Cyclization of Enyne-allenes: Experimental Evidence Supports a Stepwise MechanismThe Journal of Organic Chemistry, 2005
- Solid phase peptide synthesis utilizing 9‐fluorenylmethoxycarbonyl amino acidsInternational Journal of Peptide and Protein Research, 1990
- A General Method for the Synthesis of Diacetylenic AcidsSynthetic Communications, 1986
- Conformation of polydiacetylene macromolecules in solution: Field induced birefringence and rotational diffusion constantThe Journal of Chemical Physics, 1985
- Structure of poly(diacetylenes) in solutionMacromolecules, 1984
- Anodic Syntheses Involving ι-Monohalocarboxylic Acids1Journal of the American Chemical Society, 1956