Structurally well-characterized zinc complexes bearing imine-benzotriazole phenoxide ligands: Synthesis, photoluminescent properties and catalysis for carbon dioxide/epoxide coupling

Ting Yi Chen, Chen Yu Li, Chen Yen Tsai, Chi Huan Li, Chin Hsiang Chang, Bao Tsan Ko*, Ching Yao Chang, Chia Her Lin, Hsi Ya Huang

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)

Abstract

New imine-benzotriazole phenol ligands, RFuIBTP-H were prepared from the condensation of 3-(2H-benzotriazol-2-yl)-2-hydroxy-5-alkyl-benzaldehyde (R = C1 for alkyl = CH3; R = C8 for alkyl = C8H 17) with 1-(2-furyl)methylamine (1.1 equiv) in diethyl ether. Air-tolerant zinc complexes of bis-IBTP derivatives were synthesized and structurally characterized. The monomeric and homoleptic zinc complexes ([( C1FuIBTP)2Zn] (1), [(C8FuIBTP)2Zn] (2)) resulted from treatment of RFuIBTP-H (2.0 equiv) with ZnEt 2, in which the metal center is tetra-coordinated with two N,O-bidentate IBTP- ligands. Further reaction of 2 with 4-dimethylaminopyridine (DMAP) or 1-methylimidazole (MeIm) in stoichiometric proportion furnished the penta-coordinated monomeric zinc complexes ([( C8FuIBTP)2Zn(DMAP)] (3), [(C8FuIBTP) 2Zn(MeIm)] (4)). Optical properties and catalysis of epoxide/carbon dioxide (CO2) coupling of these IBTP-containing zinc complexes were systematically investigated. The luminescent properties showed that Zn complexes 1-4 in solution produce intense blue fluorescence with wavelength of emission maximum in a range 473-482 nm. IBTP-ligated zinc complex 2 is an active catalyst (TOF: 33.3 h-1) for the cycloaddition of CO2 with propylene oxide in the presence of n-Bu4NBr to give propylene carbonate (PC) under mild conditions. The single-component character of Zn complex 3 that is extra-coordinated with one DMAP molecule also enabled an efficient preparation of PC without a co-catalyst.

Original languageEnglish
Pages (from-to)16-25
Number of pages10
JournalJournal of Organometallic Chemistry
Volume754
DOIs
Publication statusPublished - 2014 Mar 15
Externally publishedYes

Keywords

  • Catalyst
  • CO
  • Coupling
  • Imine-benzotriazole phenoxide
  • Zinc complex

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

Fingerprint

Dive into the research topics of 'Structurally well-characterized zinc complexes bearing imine-benzotriazole phenoxide ligands: Synthesis, photoluminescent properties and catalysis for carbon dioxide/epoxide coupling'. Together they form a unique fingerprint.

Cite this