Emission and theoretical studies of Schiff-base [2+2] macrocycles derived from 2,2′-oxydianiline and zinc complexes thereof

Wang, Kuiyuan, Chen, Kai, Bian, Tiezheng, Chao, Yimin, Yamato, Takehiko, Xing, Feng, Prior, Timothy J. and Redshaw, Carl (2021) Emission and theoretical studies of Schiff-base [2+2] macrocycles derived from 2,2′-oxydianiline and zinc complexes thereof. Dyes and Pigments, 190. ISSN 0143-7208

[img] PDF (Accepted_Manuscript) - Accepted Version
Restricted to Repository staff only until 18 March 2022.
Available under License Creative Commons Attribution Non-commercial No Derivatives.

Download (11MB) | Request a copy

Abstract

The emission properties of a number of solvates of the [2 + 2] Schiff-base macrocycles {[2-(OH)-5-(R)–C 6H 2–1,3-(CH) 2][O(2-C 6H 4N) 2]} 2 (Me L 1H 2, tBu L 2H 2, Cl L 3H 2), formed by reacting 2,6-dicarboxy-4-R-phenol with 2,2′-oxydianiline (2-aminophenylether), (2-NH 2C 6H 4) 2O, have been investigated. Macrocycles L 1−3H 2 exhibited different maximum emission wavelengths in different solvents, from λ max at 508 nm (in acetonitrile) to 585 nm (in dichloromethane). DFT studies on systems L 1−3H 2 involving solvents of different polarity (DMF versus n-hexane) indicated that the energy level gap increases with solvent polarity in line with the observed hypochromic shifts. Reaction of macrocycle L 1H 2 with three equivalents of ZnBr 2, in the presence of Et 3N, affords the complex [(ZnBr)(ZnNCMe)L 1] 2[ZnBr 4]·2.5MeCN (1·2.5MeCN). In the case of L 2H 2, reaction with two equivalents of ZnBr 2 affords [(ZnBr)L 2H 2][ZnBr 3NCMe]·3MeCN (2·3MeCN), whilst in the presence of two equivalents of Et 3N, work-up led to the isolation of the complex [(ZnBr) 2L 2]·4.5MeCN (3·4.5MeCN). The molecular structures of 1, 2 and 3 are reported, together with their emission behaviour.

Item Type: Article
Uncontrolled Keywords: dft studies,emission,macrocycle,schiff-base,solvents,chemical engineering(all),process chemistry and technology ,/dk/atira/pure/subjectarea/asjc/1500
Faculty \ School: Faculty of Science > School of Chemistry
Related URLs:
Depositing User: LivePure Connector
Date Deposited: 20 Mar 2021 00:54
Last Modified: 13 May 2021 16:19
URI: https://ueaeprints.uea.ac.uk/id/eprint/79517
DOI: 10.1016/j.dyepig.2021.109300

Actions (login required)

View Item View Item