Light-Controlled Regioselective Synthesis of Fullerene Bis-Adducts.,Angewandte Chemie International Edition

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Light-Controlled Regioselective Synthesis of Fullerene Bis-Adducts.
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2020-07-28 , DOI: 10.1002/anie.202009235
Luka Ðorđević _{1,

2,

3} , Lorenzo Casimiro _{4,

5,

6} , Nicola Demitri ₇ , Massimo Baroncini _{4,

8} , Serena Silvi _{4,

5} , Francesca Arcudi _{1,

2} , Alberto Credi _{4,

9} , Maurizio Prato _{1,

10,

11}

Affiliation

Department of Chemical and Pharmaceutical Sciences & INSTM, UdR Trieste, University of Trieste, via Licio Giorgieri 1, 34127, Trieste, Italy.
Present address: Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL, 60208, USA.
Present address: Simpson Querrey Institute, Northwestern University, 303 E. Superior, Chicago, IL, 60611, USA.
CLAN-Center for Light Activated Nanostructures, Università di Bologna and Consiglio Nazionale delle Ricerche, via Gobetti 101, 40129, Bologna, Italy.
Dipartimento di Chimica "G. Ciamician", Università di Bologna, via Selmi 2, 40127, Bologna, Italy.
Present address: Supramolecular and Macromolecular Photochemistry and Photophysics, ENS Paris-Saclay, CNRS, Université Paris-Saclay, 61 Avenue du Président Wilson, 94235, Cachan, France.
Elettra-Sincrotrone Trieste, S.S. 14 Km 163.5 in Area Science Park, 34149, Basovizza, Italy.
Dipartimento di Scienze e Tecnologie Agro-alimentari, Università di Bologna, viale Fanin 44, 40127, Bologna, Italy.
Dipartimento di Chimica Industriale "Toso Montanari", Università di Bologna, viale del Risorgimento 4, 40136, Bologna, Italy.
Center for Cooperative Research in Biomaterials (CIC biomaGUNE), Basque Research and Technology Alliance (BRTA), Paseo de Miramón 182, 20014, Donostia San Sebastián, Spain.
Basque Foundation for Science, Ikerbasque, Bilbao, 48013, Spain.

Multi‐functionalization and isomer‐purity of fullerenes are crucial tasks for the development of their chemistry in various fields. In both current main approaches—tether‐directed covalent functionalization and supramolecular masks—the control of regioselectivity requires multi‐step synthetic procedures to prepare the desired tether or mask. Herein, we describe light‐responsive tethers, containing an azobenzene photoswitch and two malonate groups, in the double cyclopropanation of [60]fullerene. The formation of the bis‐adducts and their spectroscopic and photochemical properties, as well as the effect of azobenzene photoswitching on the regiochemistry of the bis‐addition, have been studied. The behavior of the tethers depends on the geometry of the connection between the photoactive core and the malonate moieties. One tether lead to a strikingly different adduct distribution for the E and Z isomers, indicating that the covalent bis‐functionalization of C₆₀ can be controlled by light.

中文翻译：

富勒烯双加合物的光控区域选择性合成。

富勒烯的多功能化和异构体纯度是其在各个领域化学发展的关键任务。在当前的两种主要方法（系链导向的共价官能化和超分子掩膜）中，区域选择性的控制都需要多步合成程序来制备所需的系链或掩膜。在本文中，我们描述了在[60]富勒烯的双环丙烷化反应中包含偶氮苯光电开关和两个丙二酸酯基团的光响应性链。研究了双加合物的形成及其光谱和光化学性质，以及偶氮苯光开关对双加合物的区域化学的影响。系链的行为取决于光敏核与丙二酸部分之间连接的几何形状。E和Z的异构体，表明C ₆₀的共价双官能化可以通过光控制。

更新日期：2020-07-28

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