Synthesis and Characterization of Cruciform-Conjugated Molecules Based on Tetrathiafulvalene
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- 作者：Mikkel Vestergaard ; Karsten Jennum ; Jakob Kryger Srensen ; Kristine Kilså ; Mogens Brndsted Nielsen
- 刊名：Journal of Organic Chemistry
- 出版年：2008
- 出版时间：April 18, 2008
- 年：2008
- 卷：73
- 期：8
- 页码：3175 - 3183
- 全文大小：317K
- 年卷期：v.73,no.8(April 18, 2008)
- ISSN：1520-6904
文摘
Stepwise acetylenic scaffolding provides cruciform-conjugated molecules with vertically disposed
-systems, one being an extended tetrathiafulvene (TTF) unit. Two synthetic routes for a cruciform dimerincorporating a total of two extended TTFs was developed, employing either an oxidative Hay couplingreaction as the final dimerization step or as one of the initial steps. Both routes take advantage of readyaccess to new mono- and diethynylbenzene building blocks incorporating a variety of other functionalitites.The redox and optical properties of the cruciform molecules were investigated by cyclic and differentialpulse voltammetries and UV-vis absorption spectroscopy. The access to multiple redox states rendersthe molecules attractive candidates as wires, or possibly transistors, for molecular electronics. Generationof a quinoid structure by oxidation is supported by density functional theory calculations.
-systems, one being an extended tetrathiafulvene (TTF) unit. Two synthetic routes for a cruciform dimerincorporating a total of two extended TTFs was developed, employing either an oxidative Hay couplingreaction as the final dimerization step or as one of the initial steps. Both routes take advantage of readyaccess to new mono- and diethynylbenzene building blocks incorporating a variety of other functionalitites.The redox and optical properties of the cruciform molecules were investigated by cyclic and differentialpulse voltammetries and UV-vis absorption spectroscopy. The access to multiple redox states rendersthe molecules attractive candidates as wires, or possibly transistors, for molecular electronics. Generationof a quinoid structure by oxidation is supported by density functional theory calculations.