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Journal of Chemical Sciences

, 130:117 | Cite as

Influence of position of methoxy groups in Zn-methoxyphenylporphyrins

  • Bishnu Prasad Borah
  • Jagannath Bhuyan
Regular Article

Abstract

The crystal structure of the compound, Zn(II) 5,10,15,20-tetrakis(meta-methoxyphenyl)porphyrin chloroform trisolvate, \([\hbox {ZnT}(m\hbox {-OCH}_{3})\hbox {PP}]{\cdot } 3\hbox {CHCl}_{3}\) 1 reveals that it forms a weak one-dimensional chain structure through interaction between Zn of porphyrin and the oxygen atom of the methoxy group of a neighbouring porphyrin. The zinc–oxygen interaction observed in compound 1 is compared with Zn(II) 5,10,15,20-tetrakis(para-methoxyphenyl)porphyrin \([\hbox {ZnT}(p\hbox {-OCH}_{3})\hbox {PP}]\) 2 and Zn(II) 5,10,15,20-tetrakis(3,4,5-tri-methoxyphenyl)porphyrin \([\hbox {ZnT}(3,4,5\hbox {-triOCH}_{3})\hbox {PP}]\) 3 to understand the preferred methoxy-position of interaction. The strength of the non-covalent zinc–oxygen (methoxy group of a neighboring porphyrin) interaction in compound 1 is in between that of similar interactions observed in compounds 2 and 3. The Mulliken charge analysis using theoretical calculation at the DFT level shows that the meta-methoxy oxygen has a higher probability of binding to the metal than the para-methoxy oxygen. In the presence of nucleophiles, the formation of one-dimensional chain structure stops due to the binding of the nucleophiles to the metal zinc. The photoluminescence and differential scanning calorimetric studies were also performed for compound 1.

Graphical Abstract

SYNOPSIS A zinc porphyrin \([\hbox {ZnT}(m\hbox {-OCH}_{3})\hbox {PP}]{\cdot } 3\hbox {CHCl}_{3}\) 1 has been synthesized and structurally characterized using single crystal X-ray diffraction and other spectroscopic methods. The crystal structure of 1 shows a weak interaction between Zn of porphyrin and the oxygen atom of the methoxy group of a neighbouring porphyrin. The Zn-oxygen interaction observed in compound 1 is compared with Zn-oxygen interaction present in other methoxy-substituted porphyrins \([\hbox {ZnT}(p\hbox {-OCH}_{3})\hbox {PP}]\) 2 and [ZnT(3,4, 5-\(\hbox {triOCH}_{3})\hbox {PP}\)] 3.

Keywords

Porphyrin coordination polymer zinc UV-Visible spectra X-ray crystallography 

Notes

Acknowledgements

JB acknowledges SERB, DST, New Delhi for funding (YSS/2015/000394). Authors thank Dr. Md. Harunar Rashid, Department of Chemistry, Rajiv Gandhi University, Itanagar for allowing to use the fluorescence spectrophotometer.

Supplementary material

12039_2018_1516_MOESM1_ESM.pdf (438 kb)
Supplementary material 1 (pdf 438 KB)

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Copyright information

© Indian Academy of Sciences 2018

Authors and Affiliations

  1. 1.Department of ChemistryNorth Eastern Regional Institute of Science and Technology (NERIST)NirjuliIndia

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