Improving the Property-Function Tuning Range of Thiophene Materials via Facile Synthesis of Oligo/Polythiophene-S-Oxides and Mixed Oligo/Polythiophene-S-Oxides/Oligo/Polythiophene-S,S-Dioxides

Di Maria Francesca; Zangoli Mattia; Palama Ilaria Elena; Fabiano Eduardo; Zanelli Alberto; Monari Magda; Perinot Andrea; Caironi Mario; Maiorano Vincenzo; Maggiore Antonio; Pugliese Marco; Salatelli Elisabetta; Gigli Giuseppe; Viola Ilenia; Barbarella Giovanna

首页> 外文期刊>Advanced Functional Materials >Improving the Property-Function Tuning Range of Thiophene Materials via Facile Synthesis of Oligo/Polythiophene-S-Oxides and Mixed Oligo/Polythiophene-S-Oxides/Oligo/Polythiophene-S,S-Dioxides

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Improving the Property-Function Tuning Range of Thiophene Materials via Facile Synthesis of Oligo/Polythiophene-S-Oxides and Mixed Oligo/Polythiophene-S-Oxides/Oligo/Polythiophene-S,S-Dioxides

机译：通过低聚/聚噻吩-S-氧化物和混合低聚/聚噻吩-S-氧化物/低聚/聚噻吩-S，S-二氧化物的简便合成来提高噻吩材料的性能调节范围

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A platform is described for the first time for the facile synthesis of oligo-and polythiophene-S-oxides and the corresponding -S,S-dioxides in short times, mild conditions, high yields. Employing ultrasound assistance, brominated thiophenes are selectively mono-or dioxygenated at room temperature. These building blocks are then combined with metalated thiophenes via microwave-assisted cross-coupling reactions through a "Lego-like" strategy to afford unprecedented oligo/polythiophene-S-oxides and mixed -S-oxides/-S,S-dioxides. It is demonstrated that depending on the number, type, and sequence alternation of nonoxygenated, monooxygenated, and dioxygenated thiophene units a very wide property-function tuning can be achieved spanning from frontier orbital energies and energy gaps, to charge transport characteristics and supramolecular H-bonding interactions with specific proteins inside live cells.

机译：首次描述了一个平台，可在短时间内，温和条件下以高收率轻松合成低聚和聚噻吩-S-氧化物以及相应的-S，S-二氧化物。利用超声辅助，溴化噻吩在室温下被选择性地单或双加氧。然后通过“类乐高”策略通过微波辅助的交叉偶联反应将这些结构单元与金属化的噻吩结合，以提供前所未有的低聚/聚噻吩-S-氧化物和混合的-S-氧化物/ -S，S-二氧化物。结果表明，根据非氧，单氧和双氧噻吩单元的数量，类型和序列的不同，可以实现非常宽泛的性能函数调节，范围从前沿的轨道能量和能隙到电荷传输特性和超分子H-与活细胞内特定蛋白质的键相互作用。

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来源
《Advanced Functional Materials》 |2016年第38期|6970-6984|共15页
作者
Di Maria Francesca; Zangoli Mattia; Palama Ilaria Elena; Fabiano Eduardo; Zanelli Alberto; Monari Magda; Perinot Andrea; Caironi Mario; Maiorano Vincenzo; Maggiore Antonio; Pugliese Marco; Salatelli Elisabetta; Gigli Giuseppe; Viola Ilenia; Barbarella Giovanna;
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Univ Salento, Dpt Math & Phys Ennio De Giorgi, I-40129 Bologna, Italy|CNR, ISOF, I-40129 Bologna, Italy;

CNR, ISOF, I-40129 Bologna, Italy|CNR, Mediteknol, I-40129 Bologna, Italy;

Univ Salento, CNR NANOTEC, Inst Nanotechnol, Campus Ecotekne, I-73100 Lecce, Italy;

UNILE IIT, CNR NANO ECMT, I-73100 Lecce, Italy|UNILE IIT, Ctr Biomol Nanotechnol, I-73100 Lecce, Italy;

CNR, ISOF, I-40129 Bologna, Italy|CNR, Mediteknol, I-40129 Bologna, Italy;

Univ Bologna, Dpt Chem Giacomo Ciamician, I-40126 Bologna, Italy;

Politecn Milan, Dpt Phys, I-20133 Milan, Italy;

Ist Italiano Tecnol, Ctr Nano Sci & Technol, PoliMi, I-20133 Milan, Italy;

Univ Salento, CNR NANOTEC, Inst Nanotechnol, Campus Ecotekne, I-73100 Lecce, Italy;

Univ Salento, Dpt Math & Phys Ennio De Giorgi, I-40129 Bologna, Italy;

Echolight Srl, R&D Dpt, Campus Ecotekne, I-73100 Lecce, Italy;

Univ Bologna, Dpt Ind Chem Toso Montanari, I-40136 Bologna, Italy;

Univ Salento, Dpt Math & Phys Ennio De Giorgi, I-40129 Bologna, Italy|Univ Salento, CNR NANOTEC, Inst Nanotechnol, Campus Ecotekne, I-73100 Lecce, Italy;

Sapienza Univ, CNR NANOTEC, I-00185 Rome, Italy|Sapienza Univ, Dpt Phys, I-00185 Rome, Italy;

CNR, ISOF, I-40129 Bologna, Italy|CNR, Mediteknol, I-40129 Bologna, Italy;

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Improving the Property-Function Tuning Range of Thiophene Materials via Facile Synthesis of Oligo/Polythiophene-S-Oxides and Mixed Oligo/Polythiophene-S-Oxides/Oligo/Polythiophene-S,S-Dioxides

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