Synthesis and photophysical properties of 2,3,4,5-tetraphenyl-1-n-octyl-1-monophosphole

被引：10
作者：
Petrov, A., V [1 ]
Zagidullin, A. A. [1 ]
Burganov, T., I [1 ]
Shatalova, N., I [2 ]
Katsyuba, S. A. [1 ]
Milyukov, V. A. [1 ]
机构：
[1] Russian Acad Sci, Kazan Sci Ctr, Fed Res Ctr, AE Arbuzov Inst Organ & Phys Chem, 8 Ul Akad Arbuzova, Kazan 420088, Russia
[2] Kazan Natl Res Technol Univ, 68 Ul K Marksa, Kazan 420015, Russia
来源：
RUSSIAN CHEMICAL BULLETIN | 2019年 / 68卷 / 02期
关键词：
phosphorus heterocycles; phosphole; luminescence; conjugation effects; Raman spectroscopy; PI-CONJUGATED MATERIALS; ELECTRONIC-PROPERTIES; FLUORESCENT-PROBE; RAMAN INTENSITY; ORGANOPHOSPHORUS; PHOSPHOLES; PARTICIPATION; DESIGN; OXIDE; RISE;
D O I：
10.1007/s11172-019-2406-6
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A new method for the preparation of 2,3,4,5-tetraphenyl-1-octyl-1-monophosphole was developed. It was shown that the reaction of n-octyl chloride with a mixture of sodium 1,2,3-tri- and 1-monophospholides obtained by refluxing sodium polyphosphides with diphenylacetylene resulted in the formation of exclusively 1-n-octyl-1-monophosphole. The photophysical properties of 1-n-octyl-1-monophosphole were studied by electron absorption and emission spectroscopy. According to the Raman spectroscopy data, the phenyl moieties of this molecule are efficiently conjugated with the diene system of the heterocycle leading to the appearance of the corresponding absorption and emission bands in the visible spectral range.
引用
收藏
页码：445 / 448
页数：4
相关论文
共 40 条
[1]   Organophosphorus π-conjugated materials [J].
Baumgartner, Thomas ;
Reau, Regis .
CHEMICAL REVIEWS, 2006, 106 (11) :4681-4727
[2]   Insights on the Design and Electron-Acceptor Properties of Conjugated Organophosphorus Materials [J].
Baumgartner, Thomas .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (05) :1613-1622
[3]   Alkali and transition metal phospholides [J].
Bezkishko, I. A. ;
Zagidullin, A. A. ;
Milyukov, V. A. ;
Sinyashin, O. G. .
RUSSIAN CHEMICAL REVIEWS, 2014, 83 (06) :555-574
[4]   An unusual reaction of cyclopropenylphosphonium bromide with sodium polyphosphides - A novel approach to sodium 3,4,5-triphenyl-1, 2-diphosphacyclopentadienide [J].
Bezkishko, Ilya ;
Miluykov, Vasily ;
Kataev, Alexander ;
Litvinov, Igor ;
Krivolapov, Dmitry ;
Sinyashin, Oleg ;
Hey-Hawkins, Evamarie .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2008, 693 (21-22) :3318-3320
[5]   Interaction of sodium pentaphospholide with dimethyl acetylenedicarboxylateA simple route to sodium 2,3,4,5-tetra(methylcarboxy)-monophospholide [J].
Bezkishko, Ilya ;
Zagidullin, Almaz ;
Petrov, Andrey ;
Miluykov, Vasili ;
Sinyashin, Oleg .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2016, 191 (11-12) :1425-1426
[6]   One-pot synthesis of aryl-substituted 1,2,3-triphospholide anions [J].
Bezkishko, Ilya A. ;
Zagidullin, Almaz A. ;
Petrov, Andrey V. ;
Miluykov, Vasili A. ;
Burganov, Timur I. ;
Katsyuba, Sergey A. ;
Sinyashin, Oleg G. .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2017, 844 :1-7
[7]   The influence of different substituents on the geometrical changes in the heterocyclic moiety of 1,2-diphospholes [J].
Burganov, T. I. ;
Zagidullin, A. A. ;
Katsyuba, S. A. ;
Miluykov, V. A. ;
Sinyashin, O. G. .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2016, 191 (11-12) :1646-1649
[8]  
Burganov TI, 2015, RUSS CHEM B+, V64, P1896
[9]   Comparative Study of Conjugational Effects in 3,4,5-Triaryl-1-R-1,2-Diphospholes and 3,4,5-Triaryl-1,2-Diphosphacyclopentadienide-Anions [J].
Burganov, Timur ;
Zagidullin, Almaz ;
Oshchepkova, Elena ;
Katsyuba, Sergey ;
Miluykov, Vasili ;
Sinyashin, Oleg .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2015, 190 (5-6) :858-862
[10]   π-Conjugated phospholes and their incorporation into devices: components with a great deal of potential [J].
Duffy, M. P. ;
Delaunay, W. ;
Bouit, P. -A. ;
Hissler, M. .
CHEMICAL SOCIETY REVIEWS, 2016, 45 (19) :5296-5310
1234