Dynamic chirality, chirality transfer and aggregation behaviour of dithienylethene switchesde Jong, J. J. D., van Rijn, P., Tiemersma-Wegeman, T. D., Lucas, L. N., Browne, W. R., Kellogg, R. M., Uchida, K., Van Esch, J. H. & Feringa, B. L., 1-Sep-2008, In : Tetrahedron. 64, 36, p. 8324-8335 12 p.
Research output: Contribution to journal › Article › Academic › peer-review
- Polymer Chemistry and Bioengineering
- Chemistry of (Bio)organic Materials and Devices
- Synthetic Organic Chemistry
- Stratingh Institute for Chemistry
- Zernike Institute for Advanced Materials
- Nanobiotechnology and Advanced Therapeutic Materials (NANOBIOMAT)
- Restoring Organ Function by Means of Regenerative Medicine (REGENERATE)
The synthesis and characterisation of a series of chiral and achiral low molecular weight organogelators (LMWGs) based on bis-amide substituted dithienylethene photochromic switches is reported. The LMWGs gelate a range of solvents depending on the specific functionalisation of the hydrogen bonding amide groups. In mixtures Of Chiral and achiral LMWGs the Steteochemical outcome of the chiral aggregation is determined by the chiral LMWG molecules in most cases. However, for the first time we demonstrate that the stereochemical outcome of the aggregation can be influenced by the achiral LWMG molecules in some cases. Furthermore specific pi-pi (and/or van der Waals) interactions of chiral LMWGs 1-3o with the solvent allow the solvent to influence the control of chirality of aggregation. This influence of the solvent has a dramatic effect on whether four- or two-gel states are available. (C) 2008 Published by Elsevier Ltd.
|Number of pages||12|
|Publication status||Published - 1-Sep-2008|
- supramolecular, photochromic switching, diarylethene, amide gel, SELF-ASSEMBLING ORGANOGELS, SYNTHETIC RECEPTORS, MOLECULAR SWITCHES, GELATORS, DITHIENYLCYCLOPENTENES, ORGANIZATION, EFFICIENCY, DIRECTION, DESIGN, GELS