Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 14, Issue 2, Pages 513-521Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200700950
Keywords
charge mobility; circular dichroism; oligonucleotides; photoluminescence; thiophene
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Quaterthiophene-dinucleotide conjugates (5')TA(3')-t4-(3')AT(5'), (5')AA(3')- t4-(3')AA(5'), and (TT3')-T-5'-t4-(TT5')-T-3' (TA: thymidine-adenosine, AA: adenosine-adenosine, TT: thymidine-thymidine) were synthesized and analyzed by a combination of spectroscopy and microscopy, electrical characterization, and theoretical calculations. Circular dichroism (CD) experiments demonstrated a transfer of chirality from the dinucleotides to quaterthiophene at high ionic strength and in cast films. The films were photoluminescent and electroactive. CD and photoluminescence spectra and current density/voltage plots (measured under dynamic vacuum) displayed significant variation on changing the dinucleotide scaffold. Molecular mechanics and molecular dynamics calculations indicated that the conformation and packing modes of the conjugates are the result of a balance between intra- and intermolecular nucleobase-thiophene stacking interactions and intramolecular hydrogen bonding between the nucleobases.
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