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To Loop or Not to Loop: Influence of Hinge Flexibility on Self‐Assembly Outcomes for Acridine‐Based Triazolylpyridine Chelates with Zinc(II), Iron(II), and Copper(II)
Author(s) -
Miron Caitlin E.,
Fleischel Olivier,
Petitjean Anne
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.201803732
Subject(s) - amide , supramolecular chemistry , hinge , chelation , chemistry , zinc , copper , self assembly , metal ions in aqueous solution , flexibility (engineering) , metal , materials science , crystallography , combinatorial chemistry , inorganic chemistry , organic chemistry , crystal structure , physics , mathematics , statistics , classical mechanics
Abstract Coordination‐driven self‐assembly has been established as an effective strategy for the efficient construction of intricate architectures in both natural and artificial systems, for applications ranging from gene regulation to metal–organic frameworks. Central to these systems is the need for carefully designed organic ligands, generally with rigid components, that can undergo self‐assembly with metal ions in a predictable manner. Herein, we report the synthesis and study of three novel organic ligands that feature 3,6‐disubstituted acridine as a rigid spacer connected to two 2‐(1,2,3‐triazol‐4‐yl)pyridine “click” chelates through hinges of the same length but differing flexibility. The flexibility of these “three‐atom” hinges was modulated by i) moving from secondary to tertiary amide functional groups and ii) replacing an sp 2 amide carbon with an sp 3 methylene carbon. In an effort to understand the role of hinge flexibility in directing self‐assembly into mononuclear loops or dinuclear cylinders, the impact of these changes on self‐assembly outcomes with zinc(II), iron(II), and copper(II) ions is described.