Design and Synthesis of Multipath Compact Cyclophanes for Quantum Interference Studies

IF 2.5 3区 化学 Q2 CHEMISTRY, ORGANIC European Journal of Organic Chemistry Pub Date : 2024-11-06 DOI:10.1002/ejoc.202400914
Salome L. Heim, Almudena Gallego, Valeria Bertozzi, Sebastiaan van der Poel, Luca Ornago, Alessandro Prescimone, Herre S. J. van der Zant, Marcel Mayor
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Abstract

To investigate interference phenomena and con­duc­tance properties in mechanically controlled break junctions (MCBJs), macrocycles 1 and 2 (BMCs: for BenzeneMacroCycles), containing a meta-substituted benzene moiety with solubilizing tert-butyl groups, as well as structures 3 and 4 (TMCs: for ThiopheneMacroCycles), featuring 2,5-connected 3,4-hexyl-thio­phene corners, were synthesized. Macrocycles 1 and 2 respect­ively 3 and 4 differ in the positions of the acetyl-protected sulfur anchoring groups, which impacts both, the individual transport efficiency of their parallel electronic pathways and their overall molecular wire lengths. All macrocycles were synthesized based on a series of Sonogashira cross-coupling reactions. For 3 and 4, a 2-(4-pyridin­yl)ethyl protecting group for the sulfur atoms was successful, while for macrocycles 1 and 2 the more common tert-butyl protecting group did the job. To our delight, proof-of-concept charge transport studies conducted in an MCBJ setup demon­strated the expected trends regarding improved conductance intensities for the TMCs compared to the BMCs. Furthermore, the corres­ponding molecular plateaus from the breaking experiments were in the expected length range of the S-S distances for all compounds. We also found that the overall conductance seems to follow a more complex transport mechanism than just the sum of contributions from both channels.
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设计和合成用于量子干涉研究的多径紧凑环烷
为了研究机械控制断裂结(MCBJ)中的干涉现象和传导特性,我们合成了含有元取代苯分子和增溶叔丁基的大环 1 和 2(BMC:代表苯大环),以及具有 2,5 连接的 3,4-hexyl-thiophene 角的结构 3 和 4(TMC:代表噻吩大环)。大环 1 和大环 2、大环 3 和大环 4 在乙酰基保护的硫锚定基团的位置上有所不同,这既影响了平行电子通路的传输效率,也影响了它们的整体分子线长度。所有大环都是通过一系列索诺伽希拉交叉偶联反应合成的。对于 3 号和 4 号大环,硫原子上的 2-(4-吡啶基)乙基保护基团取得了成功,而对于 1 号和 2 号大环,更常见的叔丁基保护基团则发挥了作用。令我们欣喜的是,在 MCBJ 设置中进行的概念验证电荷传输研究表明,与 BMC 相比,TMC 的电导强度出现了预期的改善趋势。此外,所有化合物在断裂实验中产生的相应分子高原都在 S-S 距离的预期长度范围内。我们还发现,整体电导似乎遵循一种更复杂的传输机制,而不仅仅是两个通道的贡献之和。
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来源期刊
CiteScore
5.40
自引率
3.60%
发文量
752
审稿时长
1 months
期刊介绍: The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.
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