Molecular Properties of 9,10-Phenanthrenequinone and Benzil

Chemical Research in Chinese Universities ›› 2009, Vol. 25 ›› Issue (6): 950-956.

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Molecular Properties of 9,10-Phenanthrenequinone and Benzil

Muddasir Hanif, LU Ping, GU Cheng, WANG Zhi-ming, YANG Shu-min, YANG Bing, WANG Chun-lei and MA Yu-guang*

Key Lab for Supramolecular Structure and Materials, Jilin University, Changchun 130012, P. R. China

Received:2008-09-17 Revised:2008-12-11 Online:2009-11-25 Published:2010-01-25
Contact: MA Yu-guang. E-mail: ygma@jlu.edu.cn
Supported by:
Supported by National Natural Science Foundation of China(Nos.20704016, 20573040, 20474024, 20125421, 90101026, 50303007) and Ministry of Education(No.20070183202).

Abstract

Abstract:

9,10-Phenanthrenequinone(PQ) and benzil are important α-diketones. This manuscript explains the first comparison of PQ and benzil molecular properties. We have used ¹H NMR, ¹³C NMR, ¹H-¹H COSY, HMBC, HMQC, UV-Vis absorption and emission, CV and TGA experiments to study PQ and benzil that provided the following novel results. (1) The ¹H NMR(CDCl₃) of PQ show δ 8.19(H₁), 8.02(H₄), 7.72(H₃), 7.47(H₂) instead of an earlier reported δ 8.25(H₄), 8.08(H₁), 7.80(H₂), 7.55(H₃); (2) in the ¹³C NMR(CDCl₃), the C₉/C₁₀(C=O) signal of PQ appears upfield(δ 180.3) compared to C₉/C₁₀(C=O) signal of benzil(δ 194.5), which shows higher electrophilic character(more attractive for nucleophiles) of C₉/C₁₀(C=O) of benzil; (3) the first λ_max for the UV-Vis absorption and emission of PQ are blue-shifted compared to benzil despite increased conjugation attributed to the different symmetries(C_2v for PQ and C_2h for Benzil) of the two molecules; (4) the emission spectrum of benzil is broader compared to that of PQ due to slower relaxation of the excited state; (5) The CV study shows that PQ and benzil are good electron acceptors and PQ shows a better reduction process than benzil due to an extra ring that provides stability for the reduced species(mono or diradical anions); (6) TGA shows the higher thermal stability of PQ than benzil attributed to the presence of phenanthrene unit in PQ.

Key words: 9,10-Phenanthrenequinone; Benzil; Molecular property; Electrochemistry

Muddasir Hanif, LU Ping, GU Cheng, WANG Zhi-ming, YANG Shu-min, YANG Bing, .... Molecular Properties of 9,10-Phenanthrenequinone and Benzil[J]. Chemical Research in Chinese Universities, 2009, 25(6): 950-956.

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Molecular Properties of 9,10-Phenanthrenequinone and Benzil

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