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Synchronized “click” and templated synthesis of a fluorescent pyrene crown ether

DOI: 10.1002/ejoc.201900125 DOI Help

Authors: Yvonne Choo (Newcastle University) , Paul Waddell (Newcastle University) , Andrew Benniston (Newcastle University)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: European Journal Of Organic Chemistry

State: Published (Approved)
Published: February 2019

Abstract: The reaction of 6,8‐bisethynylpyrene‐2‐carboxylic acid methyl ester with 1‐azido‐2‐(2‐(2‐azidoethoxy)ethoxy)ethoxy)ethane using standard “click” chemistry produced a 1+1 crown ether (CPYR). The copper ions used both catalyse the reaction and provide a template for ensuring smooth cyclisation. The X‐ray crystal structure of the compound reveals the two triazole groups are non‐coplanar with the pyrene moiety. The triazole groups are more co‐planar with the pyrene subunit in the first‐excited singlet state as revealed by a DFT calculated molecular structure (B3LYP, 6‐311G). Partially structured emission observed in acetonitrile is consistent with the calculation result. In acetonitrile solution the macrocycle CPYR interacts with a Na+ ion to form a complex in which the ion binds with the crown and the pyrene residue.

Journal Keywords: pyrene; crown ether; click chemistry; cation binding; structure

Subject Areas: Chemistry


Instruments: I19-Small Molecule Single Crystal Diffraction