Novel luminescent β-ketoimine derivative of 2,1,3-benzothiadiazole: synthesis, complexation with Zn(II) and photophysical properties in comparison with related compounds

T. S. Sukhikh; D. A. Bashirov; D. S. Ogienko; N. V. Kuratieva; P. S. Sherin; M. I. Rakhmanova; E. A. Chulanova; N. P. Gritsan; S. N. Konchenko; A. V. Zibarev

doi:10.1039/C6RA06547C

Novel luminescent β-ketoimine derivative of 2,1,3-benzothiadiazole: synthesis, complexation with Zn(ii) and photophysical properties in comparison with related compounds†

T. S. Sukhikh,^a D. A. Bashirov,^ab D. S. Ogienko,^a N. V. Kuratieva,^ab P. S. Sherin,^bc M. I. Rakhmanova,^a E. A. Chulanova,^bd N. P. Gritsan,^de S. N. Konchenko*^ab and A. V. Zibarev^ef

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* Corresponding authors

^a Nikolaev Institute of Inorganic Chemistry, Siberian Branch, Russian Academy of Sciences, 630090 Novosibirsk, Russia
E-mail: konch@niic.nsc.ru

^b Department of Natural Sciences, Novosibirsk State University, 630090 Novosibirsk, Russia

^c International Tomography Centre, Siberian Branch, Russian Academy of Sciences, 630090 Novosibirsk, Russia

^d Voevodsky Institute of Chemical Kinetics and Combustion, Siberian Branch, Russian Academy of Sciences, 630090 Novosibirsk, Russia

^e Department of Physics, Novosibirsk State University, 630090 Novosibirsk, Russia

^f Vorozhtsov Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 630090 Novosibirsk, Russia

Abstract

A novel β-ketoimine-functionalized 2,1,3-benzothiadiazole (4-(2,1,3-benzothiadiazole-4-ylamino)pent-3-en-2-one, L2H) was synthesized and used as chelating ligand for the complexation with Zn(II) (complex ZnL2). The spectroscopic and photophysical properties of L2H and ZnL2 as well as those of previously described 4-amino-2,1,3-benzothiadiazole (L1) and its complex ZnL1 have been thoroughly studied in the crystalline state and solution. The UV-Vis absorption spectra of free ligands L1, L2H and its deprotonated form L2⁻, and complexes ZnL1 and ZnL2 were assigned on the basis of TD-DFT calculations. In contrast to ZnL2 having conventional single-band fluorescence, ZnL1 demonstrates a broad double-band purple-white fluorescence spanning the entire visible region. On the basis of careful spectroscopic studies the second band of this unusual fluorescence spectrum was attributed to the presence of traces of free ligand L1 in the crystals of complex ZnL1. The energy transfer from the excited state of ZnL1 to a free ligand L1 was revealed.

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Novel luminescent β-ketoimine derivative of 2,1,3-benzothiadiazole: synthesis, complexation with Zn(ii) and photophysical properties in comparison with related compounds†

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Novel luminescent β-ketoimine derivative of 2,1,3-benzothiadiazole: synthesis, complexation with Zn(II) and photophysical properties in comparison with related compounds

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