Water-soluble, electroactive, and photoluminescent quaterthiophene-dinucleotide conjugates.
Quaterthiophene-dinucleotide conjugates 5'TA3'-t4-3'AT5', 5'AA3'-t4-3'AA5', and 5'TT3'-t4-3'TT5' (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.
Alesi
Silvia
S
Consiglio Nazionale Ricerche, CNR-ISOF, Via P. Gobetti 101, 40129 Bologna, Italy.
Brancolini
Giorgia
G
Melucci
Manuela
M
Capobianco
Massimo Luigi
ML
Venturini
Alessandro
A
Camaioni
Nadia
N
Barbarella
Giovanna
G
D000241:Adenosine / Q000737:chemistry*; D004563:Electrochemistry; D006860:Hydrogen Bonding; D049449:Luminescence; D008163:Luminescent Measurements / Q000379:methods; D008958:Models, Molecular; D015394:Molecular Structure; D009711:Nucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D010777:Photochemistry; D012995:Solubility; D013056:Spectrophotometry, Ultraviolet / Q000379:methods; D013237:Stereoisomerism; D013876:Thiophenes / Q000737:chemistry*; D013936:Thymidine / Q000737:chemistry*; D014867:Water / Q000737:chemistry
D009711:Nucleotides; D013876:Thiophenes; D014867:Water; D000241:Adenosine; D013936:Thymidine