多功能电荷转移剂的合成：朝向具有确定共价官能团和保留 π 系统的单壁碳纳米管,The Journal of Physical Chemistry C

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多功能电荷转移剂的合成：朝向具有确定共价官能团和保留 π 系统的单壁碳纳米管
The Journal of Physical Chemistry C ( IF 3.3 ) Pub Date : 2021-09-07 , DOI: 10.1021/acs.jpcc.1c06282
Alphonse Fiebor ₁ , Antonio Setaro _{1,

2} , Andreas J. Achazi ₃ , Georgy Gordeev ₁ , Manuela Weber ₃ , Daniel Franz ₃ , Beate Paulus ₃ , Mohsen Adeli _{1,

4} , Stephanie Reich ₁

Affiliation

将明确定义的电荷转移剂连接到纳米材料的表面是控制其电荷密度以及调整其光学、电学和物理化学性质的有效策略。特别有趣的是电荷转移剂，它根据其构建单元的排列提供或收回电子，并承诺与 sp ²等精细纳米材料的非破坏性连接化合物。在这项工作中，我们合理地合成了具有多功能功能的分子部分。反应性锚定基团允许我们将它们连接到碳纳米管作为定义的电荷转移剂，同时保持管的 π 共轭。电荷转移剂是通过在对位和间位含有一个、两个或三个甲氧基的苯胺衍生物逐步亲核取代氰尿酰氯的一个（单取代系列）或两个（双取代系列）氯原子来合成的。甲氧基作为电子转移基团的数量和位置的变化有助于我们系统地操纵分子探针的电子和光学性质及其向单壁碳纳米管 (SWNT) 的电荷转移。通过实验和量子化学计算研究了这些分子探针的光学特性与其功能之间的相关性。虽然共轭电荷转移剂的光电特性由苯胺链段主导，但三嗪保证了非破坏性附着在 SWNT 表面的能力。这项研究是朝着通过共价 π 保留功能化生产具有所需光学和电学特性的 SWNT 迈出的一步。

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Synthesis of Multifunctional Charge-Transfer Agents: Toward Single-Walled Carbon Nanotubes with Defined Covalent Functionality and Preserved π System

The attachment of well-defined charge-transfer agents to the surface of nanomaterials is an efficient strategy to control their charge density and also to tune their optical, electrical, and physicochemical properties. Particularly interesting are charge-transfer agents that either donate or withdraw electrons depending on the arrangements of their building units and that promise a nondestructive attachment to delicate nanomaterials like sp² compounds. In this work, we rationally synthesize molecular moieties with versatile functionalities. A reactive anchor group allows us to attach them to carbon nanotubes as defined charge-transfer agents while preserving the tubes’ π-conjugation. The charge-transfer agents were synthesized through the stepwise nucleophilic substitution of either one (monosubstituted series) or two (disubstituted series) chlorine atoms of cyanuric chloride by aniline derivatives containing one, two, or three methoxy groups in the para and meta positions. Variation in the number and position of the methoxy group as an electron-transferring group helps us to manipulate the electronic and optical properties of the molecular probes and their charge transfer to the single-walled carbon nanotubes (SWNTs) systematically. The correlation between the optical properties of these molecular probes and their functionality was investigated by experiments and quantum chemical calculations. While the optoelectronic properties of the conjugated charge-transfer agents were dominated by the aniline segments, the triazine warrants the ability to nondestructively attach to the surface of SWNTs. This study is one step ahead toward the production of SWNTs with desired optical and electrical properties by covalent π-preserving functionalization.

更新日期：2021-09-16

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