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报告题目：The Rational Design of Reducing Organophotoredox Catalysts Unlocks Proton-Coupled Electron-Transfer and Atom Transfer Radical Polymerization Mechanisms

主讲人： Luca Dell’Amico, University of Padova, Italy

时间：2023年10月8日 上午10:00-11:00

地点：霞光楼220会议室

邀请人：叶俊涛 副教授

个人简介

Luca Dell’Amico completed his M.Sc. in Medicinal Chemistry at the Parma University and obtained his PhD in synthetic chemistry under the supervision of Prof. Franca Zanardi in the same university. During his PhD, he spent a ten-month research period in the group of Prof. Karl Anker Jørgensen, where he was introduced to the field of organocatalysis. Luca completed his PhD with highest honours and the Doctor Europaeus mention in 2014. Shortly after, he moved to ICIQ in Spain and joined the group of Prof. Paolo Melchiorre as a Marie-Curie Postdoctoral Fellow. In the end of 2016, he started his independent career at the Padova University as an assistant professor. Since 2022 he is associate Professor in Organic Chemistry at the same institution. His research spans from the design and study of novel organophotoredox catalysts to the investigation of stereoselective photochemical processes. He has received many awards, including Giacomo Ciamician Medal, Thieme Chemistry Journals Award, and YourJOC Talents. In 2022, he was awarded an ERC starting grant to investigate new mechanistic pathways in organophotoredox catalysis.

报告摘要

Photocatalysis has become a prominent tool in the arsenal of organic chemists to develop and (re)imagine transformations. However, only a handful of versatile organic photocatalysts (PCs) are available, hampering the discovery of new reactivities. In this talk, I will discuss the design and complete characterization of 9-aryl dihydroacridines and 12-aryl dihydrobenzoacridines as strongly reducing organic PCs. Punctual structural variations modulate their excited state properties, with a dramatic influence on their performances in photoredox defunctionalizations.

Figure 1. ATRP and PCET mechanisms unlocked by free-NH acridines.

Moreover, the presence of a free-NH moiety unlocks a catalytic proton-coupled electron transfer (PCET) mechanism, which was investigated both experimentally and in silico (Figure 1, right). Finally, the PCs also engaged in metal-free atom transfer radical polymerization (ATRP, Figure 1, left), displaying good control on the chain growth. The structure-properties relationships and mechanistic scenarios disclosed herein will open new vistas in the field of photoredox catalysis.