A New Water-Soluble Phosphorus-Dipyrromethene and Phosphorus-Azadipyrromethene Dye: PODIPY/aza-PODIPY

被引：71

作者：

Jiang, Xin-Dong ^{[1
]}

Zhao, Jiuli ^{[1
]}

Xi, Dongmei ^{[1
]}

Yu, Haifeng ^{[1
]}

Guan, Jian ^{[1
]}

Li, Shuang ^{[1
]}

Sun, Chang-Liang ^{[2
]}

Xiao, Lin-Jiu ^{[1
]}

机构：

[1] Shenyang Univ Chem Technol, Coll Appl Chem, Shenyang, Peoples R China

[2] Shenyang Univ Chem Technol, Ctr Phys & Chem Test, Shenyang 110142, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2015年 / 21卷 / 16期

关键词：

fluorescent probes; phosphorus; photophysical properties; PODIPY; water soluble; TUNABLE FLUORESCENT DYES; BODIPY DYES; ORGANOARSENIC COMPOUNDS; DIPYRRINATO COMPLEXES; CHEMISTRY; DESIGN; PROBE; BF2-AZADIPYRROMETHENES; DERIVATIVES; ACTIVATION;

D O I：

10.1002/chem.201406535

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

PODIPY and aza-PODIPY have been successfully prepared by the treatment of dipyrromethene and azadipyrromethene with POCl3 in the presence of Et3N. The new PODIPY and aza-PODIPY dyes are found to have photophysical properties. PODIPY and aza-PODIPY are water-soluble, and aza-PODIPY is suited for labeling living Hep-2 cells for imaging assays in the near-infrared region. Molecular orbital calculations show that the increase in the HOMO-LUMO band gap for the lowest energy absorption bands is observed in the new phosphorus-containing aza-PODIPY, and the HOMO and LUMO energies of aza-PODIPY are found to be higher than those of aza-BODIPY.

引用

页码：6079 / 6082

页数：4

共 73 条

[1] Experimental determination of the nN → σ* P-O interaction energy of O-equatorial C-apical phosphoranes bearing a primary amino group [J].

Adachi, Takahiro ;

Matsukawa, Shiro ;

Nakamoto, Masaaki ;

Kajiyama, Kazumasa ;

Kojima, Satoshi ;

Yamamoto, Yohsuke ;

Akiba, Kin-ya ;

Re, Suyong ;

Nagase, Shigeru .

INORGANIC CHEMISTRY, 2006, 45 (18) :7269-7277

[2] The synthesis and structural characterisation of some azo-containing phosphine chalcogenides and comparison to non-phosphorus-containing analogues [J].

Alder, MJ ;

Bates, VM ;

Cross, WI ;

Flower, KR ;

Pritchard, RG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (20) :2669-2675

[3] Singlet Oxygen Generation by Novel NIR BODIPY Dyes [J].

Awuah, Samuel G. ;

Polreis, Jason ;

Biradar, Vidya ;

You, Youngjae .

ORGANIC LETTERS, 2011, 13 (15) :3884-3887

[4] The preparation of a phosphorus doped silicon film from phosphorus containing silicon nanoparticles [J].

Baldwin, RK ;

Zou, J ;

Pettigrew, KA ;

Yeagle, GJ ;

Britt, RD ;

Kauzlarich, SM .

CHEMICAL COMMUNICATIONS, 2006, (06) :658-660

[5] Luminescent dipyrrin based metal complexes [J].

Baudron, Stephane A. .

DALTON TRANSACTIONS, 2013, 42 (21) :7498-7509

[6] Dimers of dipyrrometheneboron difluoride (BODIPY) with light spectroscopic applications in chemistry and biology [J].

Bergström, F ;

Mikhalyov, I ;

Hägglöf, P ;

Wortmann, R ;

Ny, T ;

Johansson, LBÅ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (02) :196-204

[7] Design, synthesis and photophysical studies of dipyrromethene-based materials: insights into their applications in organic photovoltaic devices [J].

Bessette, Andre ;

Hanan, Garry S. .

CHEMICAL SOCIETY REVIEWS, 2014, 43 (10) :3342-3405

[8] Activation of White Phosphorus by Low-Valent Group 5 Complexes: Formation and Reactivity of cyclo-P4 Inverted Sandwich Compounds [J].

Camp, Clement ;

Maron, Laurent ;

Bergman, Robert G. ;

Arnold, John .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (50) :17652-17661

[9] Phosphorus-containing thermotropic liquid crystalline polymers: a class of efficient polymeric flame retardants [J].

Chen, Li ;

Ruan, Chao ;

Yang, Rong ;

Wang, Yu-Zhong .

POLYMER CHEMISTRY, 2014, 5 (12) :3737-3749

[10]

Coulson D. R., 1972, INORG SYNTH, V13, P121, DOI DOI 10.1002/9780470132449.CH23

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