Jump to main content
Jump to site search
PLANNED MAINTENANCE Close the message box

Scheduled maintenance upgrade on Thursday 4th of May 2017 from 8.00am to 9.00am (BST).

During this time our websites will be offline temporarily. If you have any questions please use the feedback button on this page. We apologise for any inconvenience this might cause and thank you for your patience.


Issue 6, 2010
Previous Article Next Article

Redox-triggered switching of helical chirality of poly(phenylacetylene)s bearing riboflavin pendants

Author affiliations

Abstract

Two novel optically active poly(phenylacetylene)s bearing riboflavin (vitamin B2) residues as the pendant through different covalent linkages (poly-1 and poly-2) were prepared by the polymerization of the corresponding monomers (1 and 2) with a rhodium catalyst, and their chiroptical properties were investigated by UV-visible and circular dichroism (CD) spectroscopies. Riboflavin-linked poly-2 through the acetal linkage with the ribityl group to the phenylacetylene exhibited a relatively intense induced CD (ICD) in the polymer backbone region. The ICD was temperature-dependent, indicating that the main chain of poly-2 adopts a dynamic preferred-handed helical conformation induced by the optically active ribityl group. In contrast, poly-1 having the riboflavin pendant via the N3-methylene linker showed almost no apparent ICD due to the main-chain helical conformation, probably because the optically active ribityl group of poly-1 is located relatively far from the polymer backbone compared with poly-2. The cyclic voltammetric measurements of poly-1 and poly-2 revealed that these polymers possess reversible redox properties originating from the electron transfer process of the riboflavin pendants. The switching of the chiroptical properties in response to the redox stimuli was also investigated using a chemical reductant (Na2S2O4) and oxidant (O2).

Graphical abstract: Redox-triggered switching of helical chirality of poly(phenylacetylene)s bearing riboflavin pendants

Back to tab navigation
Please wait while Download options loads

Supplementary files

Publication details

The article was received on 11 Feb 2010, accepted on 26 Mar 2010 and first published on 20 Apr 2010


Article type: Paper
DOI: 10.1039/C0PY00044B
Citation: Polym. Chem., 2010,1, 841-848
  •   Request permissions

    Redox-triggered switching of helical chirality of poly(phenylacetylene)s bearing riboflavin pendants

    H. Iida, T. Mizoguchi, S. Oh and E. Yashima, Polym. Chem., 2010, 1, 841
    DOI: 10.1039/C0PY00044B

Search articles by author