Photochemical Functionalization of Graphene Oxide by Thiol–Ene Click Chemistry,Industrial & Engineering Chemistry Research

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Photochemical Functionalization of Graphene Oxide by Thiol–Ene Click Chemistry
Industrial & Engineering Chemistry Research ( IF 3.8 ) Pub Date : 2020-06-19 , DOI: 10.1021/acs.iecr.0c01252
Alexis Piñeiro-García _{1,

2} , Sofia M. Vega-Díaz ₁ , Ferdinando Tristán ₁ , David Meneses-Rodríguez ₃ , Gladis Judith Labrada-Delgado ₄ , Vincent Semetey ₂

Affiliation

Graphene oxide (GO) is an important platform that can be functionalized, notably because of its wide variety of functional groups. Functionalization is a critical step, leading to the production of GO-based materials for promising applications in many fields ranging from biomedicine, depollution, to energy storage. Defects introduced into the graphitic domain during graphite oxidation allow to obtain alkene groups, which can be functionalized via thiol–ene click reactions (TER). Usually, for GO functionalization by TER, thermal radical initiators have been used with disadvantages such as high reaction times and the subsequent GO reduction, losing possible oxygen functional groups that can be further used for a second functionalization. Hence, we introduce the photochemical functionalization of GO by TER, with cysteamine as the probe molecule, using a photoinitiator. The reaction was characterized by attenuated total reflection–Fourier transform infrared spectroscopy, UV spectroscopy, fluorimetry, X-ray photoelectron spectroscopy, and Raman spectroscopy. This new perspective of photoinduced TER provides advantages such as short reaction times, use of mild conditions, and avoiding a subsequent GO reduction, associated with efficient orthogonal functionalization.

中文翻译：

硫醇-烯点击化学对氧化石墨烯的光化学官能化

氧化石墨烯（GO）是一个可以进行功能化的重要平台，特别是由于其广泛的官能团。功能化是至关重要的一步，导致生产出基于GO的材料，可用于从生物医学，去污染到能量存储等许多领域的有希望的应用。在石墨氧化过程中引入石墨域的缺陷允许获得烯基，可以通过硫醇-烯点击反应（TER）。通常，对于通过TER进行的GO官能化，已经使用了热自由基引发剂，其具有诸如高反应时间和随后的GO还原的缺点，失去了可能进一步用于第二官能化的氧官能团。因此，我们使用光引发剂引入了以半胱胺为探针分子的TER对GO的光化学功能化。该反应的特征在于衰减的全反射-傅立叶变换红外光谱，UV光谱，荧光法，X射线光电子能谱和拉曼光谱。光致TER的这种新观点提供了诸如有效的正交官能化相关的优点，例如反应时间短，使用温和条件以及避免随后的GO降低。

更新日期：2020-07-22

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