Synthesis, structure, spectral and electrochemical properties of B(OR) 2-smaragdyrin complexes

Hemanta Kalita; Way Zen Lee; Mangalampalli Ravikanth

doi:10.1039/c3dt51539g

Synthesis, structure, spectral and electrochemical properties of B(OR) ₂-smaragdyrin complexes

Hemanta Kalita, Way Zen Lee, Mangalampalli Ravikanth^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

12 Citations (Scopus)

Abstract

A series of B(OR)₂-smaragdyrin complexes were synthesized by treating BF₂-smaragdyrin complex with various aliphatic and aromatic alcohols in the presence of AlCl₃ in CH₂Cl₂ at room temperature. The compounds are stable and characterized by various spectroscopic and electrochemical techniques. The X-ray structure solved for one of the B(OR)₂-smaragdyrin complex showed that the macrocycle is planar and the boron atom is in tetrahedral geometry coordinated to two pyrrole nitrogens of the macrocycle and two oxygen atoms of the axial -OR groups. ¹H NMR studies indicated that the alkoxy or aryloxy groups present on the boron atom experience the macrocyclic ring current effect and appear in the up-field region. The absorption properties of B(OR)₂-smaragdyrin complexes showed a strong absorption band at ∼700 nm along with other absorption bands in the 450-650 nm region like BF₂-smaragdyrin complex. Since B(OR)₂-smaragdyrin complexes are electron rich due to the presence of electron rich alkoxy and aryloxy groups, the B(OR) ₂-smaragdyrin complexes are easier to oxidize but difficult to reduce compared to BF₂-smaragdyrin. The B(OR)₂-smaragdyrin complexes are found to be weakly fluorescent than BF₂-smaragdyrin.

Original language	English
Pages (from-to)	14537-14544
Number of pages	8
Journal	Dalton Transactions
Volume	42
Issue number	40
DOIs	https://doi.org/10.1039/c3dt51539g
Publication status	Published - 2013 Oct 28

ASJC Scopus subject areas

Inorganic Chemistry

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10.1039/c3dt51539g

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title = "Synthesis, structure, spectral and electrochemical properties of B(OR) 2-smaragdyrin complexes",

abstract = "A series of B(OR)2-smaragdyrin complexes were synthesized by treating BF2-smaragdyrin complex with various aliphatic and aromatic alcohols in the presence of AlCl3 in CH2Cl2 at room temperature. The compounds are stable and characterized by various spectroscopic and electrochemical techniques. The X-ray structure solved for one of the B(OR)2-smaragdyrin complex showed that the macrocycle is planar and the boron atom is in tetrahedral geometry coordinated to two pyrrole nitrogens of the macrocycle and two oxygen atoms of the axial -OR groups. 1H NMR studies indicated that the alkoxy or aryloxy groups present on the boron atom experience the macrocyclic ring current effect and appear in the up-field region. The absorption properties of B(OR)2-smaragdyrin complexes showed a strong absorption band at ∼700 nm along with other absorption bands in the 450-650 nm region like BF2-smaragdyrin complex. Since B(OR)2-smaragdyrin complexes are electron rich due to the presence of electron rich alkoxy and aryloxy groups, the B(OR) 2-smaragdyrin complexes are easier to oxidize but difficult to reduce compared to BF2-smaragdyrin. The B(OR)2-smaragdyrin complexes are found to be weakly fluorescent than BF2-smaragdyrin.",

author = "Hemanta Kalita and Lee, {Way Zen} and Mangalampalli Ravikanth",

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AU - Kalita, Hemanta

AU - Lee, Way Zen

AU - Ravikanth, Mangalampalli

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N2 - A series of B(OR)2-smaragdyrin complexes were synthesized by treating BF2-smaragdyrin complex with various aliphatic and aromatic alcohols in the presence of AlCl3 in CH2Cl2 at room temperature. The compounds are stable and characterized by various spectroscopic and electrochemical techniques. The X-ray structure solved for one of the B(OR)2-smaragdyrin complex showed that the macrocycle is planar and the boron atom is in tetrahedral geometry coordinated to two pyrrole nitrogens of the macrocycle and two oxygen atoms of the axial -OR groups. 1H NMR studies indicated that the alkoxy or aryloxy groups present on the boron atom experience the macrocyclic ring current effect and appear in the up-field region. The absorption properties of B(OR)2-smaragdyrin complexes showed a strong absorption band at ∼700 nm along with other absorption bands in the 450-650 nm region like BF2-smaragdyrin complex. Since B(OR)2-smaragdyrin complexes are electron rich due to the presence of electron rich alkoxy and aryloxy groups, the B(OR) 2-smaragdyrin complexes are easier to oxidize but difficult to reduce compared to BF2-smaragdyrin. The B(OR)2-smaragdyrin complexes are found to be weakly fluorescent than BF2-smaragdyrin.

AB - A series of B(OR)2-smaragdyrin complexes were synthesized by treating BF2-smaragdyrin complex with various aliphatic and aromatic alcohols in the presence of AlCl3 in CH2Cl2 at room temperature. The compounds are stable and characterized by various spectroscopic and electrochemical techniques. The X-ray structure solved for one of the B(OR)2-smaragdyrin complex showed that the macrocycle is planar and the boron atom is in tetrahedral geometry coordinated to two pyrrole nitrogens of the macrocycle and two oxygen atoms of the axial -OR groups. 1H NMR studies indicated that the alkoxy or aryloxy groups present on the boron atom experience the macrocyclic ring current effect and appear in the up-field region. The absorption properties of B(OR)2-smaragdyrin complexes showed a strong absorption band at ∼700 nm along with other absorption bands in the 450-650 nm region like BF2-smaragdyrin complex. Since B(OR)2-smaragdyrin complexes are electron rich due to the presence of electron rich alkoxy and aryloxy groups, the B(OR) 2-smaragdyrin complexes are easier to oxidize but difficult to reduce compared to BF2-smaragdyrin. The B(OR)2-smaragdyrin complexes are found to be weakly fluorescent than BF2-smaragdyrin.

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Synthesis, structure, spectral and electrochemical properties of B(OR) ₂-smaragdyrin complexes

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CCDC 933956: Experimental Crystal Structure Determination

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Synthesis, structure, spectral and electrochemical properties of B(OR) 2-smaragdyrin complexes

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ASJC Scopus subject areas

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CCDC 933956: Experimental Crystal Structure Determination

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Synthesis, structure, spectral and electrochemical properties of B(OR) ₂-smaragdyrin complexes