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Coordination‐Driven Folding in Multi‐Zn II ‐Porphyrin Arrays Constructed on a Pillar[5]arene Scaffold
Author(s) -
Trinh Thi Minh Nguyet,
Nierengarten Iwona,
Ben Aziza Haifa,
Meichsner Eric,
Holler Michel,
Chessé Matthieu,
Abidi Rym,
Bijani Christian,
Coppel Yannick,
Maisonhaute Emmanuel,
DelavauxNicot Béatrice,
Nierengarten JeanFrançois
Publication year - 2017
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.201701622
Subject(s) - porphyrin , intramolecular force , imidazole , chemistry , alkyne , molecule , supramolecular chemistry , crystallography , folding (dsp implementation) , cyclic voltammetry , ligand (biochemistry) , azide , stereochemistry , photochemistry , electrochemistry , crystal structure , receptor , organic chemistry , electrode , biochemistry , electrical engineering , engineering , catalysis
Pillar[5]arene derivatives bearing peripheral porphyrin subunits have been efficiently prepared from a deca‐azide pillar[5]arene building block ( 17 ) and Zn II ‐porphyrin derivatives bearing a terminal alkyne function ( 9 and 16 ). For the resulting deca‐Zn II ‐porphyrin arrays ( 18 and 20 ), variable temperature NMR studies revealed an intramolecular complexation of the peripheral Zn II ‐porphyrin moieties by 1,2,3‐triazole subunits. As a result, the molecules adopt a folded conformation. This was further confirmed by UV/Vis spectroscopy and cyclic voltammetry. In addition, we have also demonstrated that the coordination‐driven unfolding of 18 and 20 can be controlled by an external chemical stimulus. Specifically, addition of an imidazole derivative ( 22 ) to solution of 18 or 20 breaks the intramolecular coordination at the origin of the folding. The resulting molecular motions triggered by the addition of the imidazole ligand mimic the blooming of a flower.