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Influence of H‐Bonding on Self‐Assembly and Tunable Dual‐Emission of Carbazole‐Based Zn(II)‐Terpyridine Metallocycles
Author(s) -
Gao Yang,
He Tingchao,
Hu Peng,
Koh Teck Ming,
Sun Handong,
Grimsdale Andrew C.
Publication year - 2014
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.201300737
Subject(s) - carbazole , terpyridine , chemistry , x ray photoelectron spectroscopy , photochemistry , crystallography , analytical chemistry (journal) , metal , organic chemistry , physics , nuclear magnetic resonance
Two carbazole derivatives with terpyridine units attached to the 3,6‐positions are synthesized, 1 with a hydrogen at the 9‐position and 2 bearing a dodecyl chain there, to evaluate the influence of H‐bonds on their self‐assembly behavior with metal ions. The unalkylated derivative 1 assembles with zinc ions to form a single product identified by NMR, electrospray ionisation mass spectrometry (ESI‐MS), and X‐ray photoelectron spectroscopy (XPS) as a pentametric metallocycle ( Zn‐1 ), whereas 2 forms a mixture of two assemblies ( Zn‐2 ). The pentamer Zn‐1 shows tunable dual emission in the blue and green regions by varying the solvent and excitation wavelength, and molecular packing studies by powder X‐ray diffractometry (XRD), transmission electron microscopy (TEM), polarising optical microscopy (POM), and atomic force microscopy (AFM) reveals a high propensity to form ordered layers. A fluorescence quenching experiment of electron‐rich Zn‐1 with C 60 shows a high association constant of K sv = 3.2 × 10 5 m −1 , suggesting effective charge transfer between Zn‐1 and C 60 molecules.