A novel 16-membered [1+1] unsymmetrical selenaaza Schiff base macrocycle, 8,9,10,11-tetrahydo-7H-dibenzo-[d,o][1,3,7,10,13]diselenatriazacyclohexadecine (5) with N3Se2 donor set, has been synthesized by cyclocondensation of di(o-formylphenylseleno)methane and diethylenetriamine. Reduction of 5 with NaBH4 afforded 6,7,8,9,10,11,12,13-octahydro-5H- dibenzo-[d,o][1,3,7,10,13]diselenatriazacyclohexadecine (6). Macrocycle, 10,11,12,13,14,15,16,26,27,28,29,30,31,32-tetradecahydrotetrabenzo[b,k,n,w][1, 13,5,9,17,21]diselenatetraazacyclotetracosine (2b) was synthesized similarly from di(o-formylphenyl)selenide and 1,3-diaminopropane followed by reduction with NaBH4. Single crystal X-ray structures of 5 and 2b have been determined. Attempted complexation reactions of 5 with Zn(II), Cd(II), Hg(II), Pd(II) and Cu(II) ions and those of 6 with Ag(I), Hg(II) and Pd(II) ions are reported. 28-Membered selenaaza macrocycle 2c on reaction with HgCl2 and NH4PF6, provided a dinuclear Hg(II) complex 9. Complex 9 has been characterized by single crystal X-ray structure.
Bibliographical noteFunding Information:
We are thankful to the Department of Science and Technology (DST), India for funding this work. Additional help from the Sophisticated Analytical Instrument Facility (SAIF), Indian Institute of Technology, Bombay, for 300 MHz NMR spectroscopy is gratefully acknowledged. We gratefully acknowledge Dr. A. Panda for help in the synthesis of the macrocyclic ligand 2b . T.C. and K.S. are also grateful to the Council of Scientific and Industrial Research, India for providing fellowship.
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- Mercurous ion
- Schiff base macrocycle