Journal
DALTON TRANSACTIONS
Volume 43, Issue 42, Pages 15915-15928Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4dt01978d
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Funding
- Ministry of Education, Culture, Sports, Science and Technology (Scientific Research on Innovative Areas Stimuli-responsive Chemical Species for the Creation of Functional Molecules) [25109505]
- Iwatani Naoji Foundation's Research Grant
- Grants-in-Aid for Scientific Research [25109505] Funding Source: KAKEN
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Five halogen substituted pyrazolates, 4-chloro-3,5-diisopropylpyrazole (4-Cl-3,5-iPr(2)pzH), 4-bromo-3,5-diisopropylpyrazole (4-Br-3,5-iPr(2)pzH), 4-iodo-3,5-diisopropylpyrazole (4-I-3,5-iPr(2)pzH), 4-chtoro-3,5-diphenylpyrazole (4-Cl-3,5-Ph(2)pzH), and 4-bromo-3,5-diphenylpyrazole (4-Br-3,5-Ph(2)pzH), were conveniently prepared by halogenation of the appropriate pyrazoles with N-halosuccinimides (NXS) (X = Cl, Br, and I) followed by complexation of the pyrazolate anions with silver(I)) nitrate. Single crystal X-ray analysis revealed either dimeric trinuclear {Ag(mu-4-X-3,5-R(2)pz)](3)}(2) (R = iPr, X = Cl, Br, and I) or trinuclear [Ag(mu-4-X 3,5-R(2)pz)](3) (R = iPr, X = I: R = Ph, X = Cl, R = Ph, X = Br) structures, the latter held together with argentophilic interactions (Ag center dot center dot center dot Ag interactions) that could also be observed in the Raman spectra. The electronegativity of the halogen substituent could be correlated with the strength of the Ag...Ag interaction and the wavelength of solid-state photoluminescence. All complexes were emissive on UV irradiation at low temperatures, with the colour of emission from the diisopropyl substituted analogues red shifted by the halogens in the order Cl (red) > Br (orange) > I (yellow). Emission from the diphenyl substituted analogues was dominated by the extended aromatic system and was largely invariant to the halogens.
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