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Synchronized “Click” and Templated Synthesis of a Fluorescent Pyrene Crown Ether
Author(s) -
Choo Yvonne S. L.,
Waddell Paul G.,
Benniston Andrew C.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900125
Subject(s) - chemistry , pyrene , acetonitrile , crown ether , click chemistry , alkoxy group , moiety , photochemistry , density functional theory , triazole , singlet state , carboxylate , ether , medicinal chemistry , stereochemistry , excited state , ion , polymer chemistry , organic chemistry , computational chemistry , physics , alkyl , nuclear physics
The reaction of methyl 6,8‐bisethynylpyrene‐2‐carboxylate 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 density functional theory (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.