Molecular and ionic complexes of pyrrolidinofullerene bearing chelating 3-pyridyl units

Dmitri V. Konarev, Salavat S. Khasanov, Alexey B. Kornev, Maxim A. Faraonov, Pavel A. Troshin, Rimma N. Lyubovskaya

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

Molecular and ionic complexes of cis-2′,5′-di(pyridin-3-yl) pyrrolidino[3′,4′:1,9](C 60-I h)[5,6]fullerene DP3FP with chlorobenzene (C 6H 5Cl), manganese(ii) tetraphenylporphyrin (Mn IITPP) and tetrakis(dimethylamino)ethylene (TDAE) have been obtained for the first time. X-ray single crystal structure determination for the crystalline DP3FP·C 6H 5Cl (1) solvate proved unambiguously its molecular structure with the cis-arrangement of chelating 3-pyridyl groups. It has been demonstrated that DP3FP easily forms self-assembled photoactive complexes with metallated porphyrins. For example, the formation of a 1:1 complex between DP3FP and zinc (ii) tetraphenylporphyrin (Zn IITPP) in cyclohexane solution (2) was evidenced using absorption spectroscopy. A successful X-ray single crystal structure determination was performed for a self-assembled triad composed of a DP3FP molecule linked with two Mn IITPP molecules in {DP3FP·(Mn IITPP) 2}·(C 6H 4Cl 2) 3 (3). A strong organic donor TDAE reduces DP3FP to the radical anion state thus forming an ionic complex (TDAE +)·(DP3FP -) ·(C 6H 4Cl 2) 1.6 (4). Optical, electronic and magnetic properties of 4 were investigated in detail. The performed studies strongly suggest that pyrrolidinofullerene DP3FP can be used as a building block in the design of various organic materials with advanced optoelectronic and/or magnetic properties.

Original languageEnglish
Pages (from-to)791-798
Number of pages8
JournalDalton Transactions
Volume41
Issue number3
DOIs
Publication statusPublished - 21 Jan 2012
Externally publishedYes

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