Varghese, Reji and Wagenknecht, Hans-Achim (2010) Non-covalent Versus Covalent Control of Self-Assembly and Chirality of Nile Red-modified Nucleoside and DNA. CHEMISTRY-A EUROPEAN JOURNAL, 16 (30). pp. 9040-9046. ISSN 0947-6539, 1521-3765
Full text not available from this repository. (Request a copy)Abstract
A DNA-based covalent versus a non-covalent approach is demonstrated to control the optical, chirooptical and higher order structures of Nile red (Nr) aggregation. Dynamic light scattering and TEM studies revealed that in aqueous media Nr-modified 2'-deoxyuridine aggregates through the co-operative effect of various non-covalent interactions including the hydrogen bonding ability of the nucleoside and sugar moieties and the pi-stacking tendency of the highly hydrophobic dye. This results in the formation of optically active nanovesicles. A left-handed helically twisted H-type packing of the dye is observed in the bilayer of the vesicle as evidenced from the optical and chirooptical studies. On the other hand, a left-handed helically twisted J-type packing in vesicles was obtained from a non-polar solvent (toluene). Even though the primary stacking interaction of the dye aggregates transformed from H -> J while going from aqueous to non-polar media, the induced supramolecular chirality of the aggregates remained the same (left-handed). Circular dichroism studies of DNA that contained several synthetically incorporated and covalently attached Nr-modified nucleosides revealed the formation of helically stacked H-aggregates of Nr but- in comparison to the noncovalent aggregates-an inversed chirality (right-handed). This self-assembly propensity difference can, in principle, be applied to other hydrophobic dyes and chromophores and thus open a DNA-based approach to modulate the primary stacking interactions and supramolecular chirality of dye aggregates.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | PERYLENE BISIMIDE DYES; PI-CONJUGATED SYSTEMS; HELICAL PYRENE-ARRAY; INTERSTRAND STACKING; SUPRAMOLECULAR ARCHITECTURES; GUANOSINE DERIVATIVES; MOLECULAR MATERIALS; PORPHYRIN ARRAYS; BUILDING-BLOCKS; ENERGY-TRANSFER; aggregation; chirality; DNA; dyes/pigments; self-assembly |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Alumni or Retired Professors > Arbeitskreis Prof. Dr. Hans-Achim Wagenknecht |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 12 Aug 2020 13:06 |
| Last Modified: | 12 Aug 2020 13:06 |
| URI: | https://pred.uni-regensburg.de/id/eprint/25399 |
Actions (login required)
 |
View Item |
