Journal
MACROMOLECULAR CHEMISTRY AND PHYSICS
Volume 215, Issue 8, Pages 753-762Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/macp.201300737
Keywords
dual emission; H-bond; long-range order; macrocycle; tunable emission
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Funding
- NTU
- National Research Foundation through CRP [5-2009-04]
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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 x 10(5)m(-1), suggesting effective charge transfer between Zn-1 and C-60 molecules.
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