Water-soluble, electroactive, and photoluminescent quaterthiophene-dinucleotide conjugates

被引：21

作者：

Alesi, Silvia ^{[1
]}

Brancolini, Giorgia ^{[1
]}

Melucci, Manuela ^{[1
]}

Capobianco, Massimo Luigi ^{[1
]}

Venturini, Alessandro ^{[1
]}

Camaioni, Nadia ^{[1
]}

Barbarellala, Giovanna ^{[1
]}

机构：

[1] CNR, ISOF, I-40129 Bologna, Italy

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2008年 / 14卷 / 02期

关键词：

charge mobility; circular dichroism; oligonucleotides; photoluminescence; thiophene;

D O I：

10.1002/chem.200700950

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：513 / 521

页数：9

共 53 条

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