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A Rotaxane Scaffold for the Construction of Multiporphyrinic Light‐Harvesting Devices
Author(s) -
DelavauxNicot Béatrice,
Ben Aziza Haifa,
Nierengarten Iwona,
Minh Nguyet Trinh Thi,
Meichsner Eric,
Chessé Matthieu,
Holler Michel,
Abidi Rym,
Maisonhaute Emmanuel,
Nierengarten JeanFrançois
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201704124
Subject(s) - porphyrin , rotaxane , supramolecular chemistry , intramolecular force , free base , click chemistry , molecular machine , photochemistry , chemistry , energy transfer , self assembly , combinatorial chemistry , materials science , nanotechnology , molecule , stereochemistry , organic chemistry , salt (chemistry) , molecular physics
A sophisticated photoactive molecular device has been prepared by combining recent concepts for the preparation of multifunctional nanomolecules (click chemistry on multifunctional scaffolds) with supramolecular chemistry (self‐assembly to prepare rotaxanes). Specifically, a clickable [2]rotaxane scaffold incorporating a free‐base porphyrin stopper has been prepared and functionalized with ten peripheral Zn(II)‐porphyrin moieties. Electrochemical investigations of the final compound revealed a peculiar behavior resulting from the intramolecular coordination of the Zn(II) porphyrin moieties to 1,2,3‐triazole units. Finally, steady state investigations of the compound combining Zn(II) and free‐base porphyrin moieties have shown that this compound is a light‐harvesting device capable of channeling the light energy from the peripheral Zn(II)‐porphyrin subunits to the core by singlet–singlet energy transfer.