Synthesis, GC-EIMS, 1H NMR, 13C NMR, Mechanistic and Thermal Studies of o-Xylylene-α,α’-bis(triphenylphosphinebromide)

Chemical Research in Chinese Universities ›› 2009, Vol. 25 ›› Issue (5): 754-759.

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Synthesis, GC-EIMS, ¹H NMR, ¹³C NMR, Mechanistic and Thermal Studies of o-Xylylene-α,α’-bis(triphenylphosphinebromide)

Muddasir Hanif, LU Ping, XU Hai, TIAN Zhi-cheng, YANG Bing, WANG Zhi-ming, TIAN Lei-lei, XU Yuan-ze, XIE Zeng-qi and MA Yu-guang*

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

Received:2008-09-16 Online:2009-09-25 Published:2009-12-07
Contact: MA Yu-guang. E-mail: ygma@jlu.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(Nos.20573040, 20474024, 20125421, 90101026 and 50303007).

Abstract

Abstract:

Organophosphorous compounds containing phosphorus as an integral part have been widely used in industry, organic synthesis and optoelectronics. o-Xylylene-α,α’-bis(triphenylphosphinebromide)(OXBTPPB) is a facile reagent to convert o-quinones(e.g., 9,10-phenanthrenequinone) into polycyclic aromatic hydrocarbons(PAHs). Herein lies an improved synthetic route to OXBTPPB. The resultant was carefully characterized with GC-EIMS, ¹H NMR, ¹³C NMR, spectroscopic techniques. The EIMS shows characteristic peaks at m/z=262.4, 183.3, 108.2, 77.1 attributed to the [C₁₈H₁₅P]^+·, [C₁₂H₈P]⁺, [C₆H₅P]⁺, [C₆H₅]⁺ ions, respectively. The ¹H and ¹³C NMR spectrum shows well resolved peaks and all the hydrogens and carbons were well-assigned via a combined study of ¹H-¹H COSY, HMBC, and HMQC experiments. The mechanism for the formation of OXBTPPB was proposed based on literature and obtained experimental data. Meanwhile, the thermal stability of OXBTPPB was evaluated with TGA analysis, and an onset decomposition temperature(T_d) was recorded at 323.6 °C.

Key words: Organophosphorous compound; o-Quinone; Molecular structure; Optoelectronics

Muddasir Hanif, LU Ping, XU Hai, TIAN Zhi-cheng, YANG Bing, WANG Zhi-ming, ...... Synthesis, GC-EIMS, ¹H NMR, ¹³C NMR, Mechanistic and Thermal Studies of o-Xylylene-α,α’-bis(triphenylphosphinebromide)[J]. Chemical Research in Chinese Universities, 2009, 25(5): 754-759.

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Synthesis, GC-EIMS, ¹H NMR, ¹³C NMR, Mechanistic and Thermal Studies of o-Xylylene-α,α’-bis(triphenylphosphinebromide)

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