Synthesis and characterization of fluoronitroaryl azo diaminobenzene chromophores

L. Ren; G. Y. Li; X. Hu; X. L. Xia; J. R. Shen; D. M. Jia

doi:10.1016/j.tetlet.2005.01.022

Synthesis and characterization of fluoronitroaryl azo diaminobenzene chromophores

L. Ren, G. Y. Li^*, X. Hu, X. L. Xia, J. R. Shen, D. M. Jia

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

7 Citations (Scopus)

Abstract

The novel fluoronitroaryl azo diaminobenzene chromophores for potential NLO applications were synthesized and the effects of the position of the fluorine group on the properties of the chromophores were investigated. These chromophores exhibit high decomposition temperatures whilst keeping molecular hyperpolarizabilities similar to those of the non-fluorinated analogues. The chromophore 2,4-diamino-4′-fluoro-3′-nitroazobenzene (2R-4F-3N-DIAMINE) shows a significant UV blue shift and a combination of good transparency, high thermal stability and nonlinearity in comparison with 2,4-diamino-2′-fluoro-5′-nitroazobenzene (2R-2F-5N-DIAMINE) and its non-fluorinated analogue 2,4-diamino-3′-nitroazobenzene (2R-3N-DIAMINE).

Original language	English
Pages (from-to)	1511-1513
Number of pages	3
Journal	Tetrahedron Letters
Volume	46
Issue number	9
DOIs	https://doi.org/10.1016/j.tetlet.2005.01.022
Publication status	Published - Feb 28 2005
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Chromophore
Fluorine
Hyperpolarizability
Nonlinear optical materials

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10.1016/j.tetlet.2005.01.022

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title = "Synthesis and characterization of fluoronitroaryl azo diaminobenzene chromophores",

abstract = "The novel fluoronitroaryl azo diaminobenzene chromophores for potential NLO applications were synthesized and the effects of the position of the fluorine group on the properties of the chromophores were investigated. These chromophores exhibit high decomposition temperatures whilst keeping molecular hyperpolarizabilities similar to those of the non-fluorinated analogues. The chromophore 2,4-diamino-4′-fluoro-3′-nitroazobenzene (2R-4F-3N-DIAMINE) shows a significant UV blue shift and a combination of good transparency, high thermal stability and nonlinearity in comparison with 2,4-diamino-2′-fluoro-5′-nitroazobenzene (2R-2F-5N-DIAMINE) and its non-fluorinated analogue 2,4-diamino-3′-nitroazobenzene (2R-3N-DIAMINE).",

keywords = "Chromophore, Fluorine, Hyperpolarizability, Nonlinear optical materials",

author = "L. Ren and Li, \{G. Y.\} and X. Hu and Xia, \{X. L.\} and Shen, \{J. R.\} and Jia, \{D. M.\}",

year = "2005",

month = feb,

day = "28",

doi = "10.1016/j.tetlet.2005.01.022",

language = "English",

volume = "46",

pages = "1511--1513",

journal = "Tetrahedron Letters",

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number = "9",

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TY - JOUR

T1 - Synthesis and characterization of fluoronitroaryl azo diaminobenzene chromophores

AU - Ren, L.

AU - Li, G. Y.

AU - Hu, X.

AU - Xia, X. L.

AU - Shen, J. R.

AU - Jia, D. M.

PY - 2005/2/28

Y1 - 2005/2/28

N2 - The novel fluoronitroaryl azo diaminobenzene chromophores for potential NLO applications were synthesized and the effects of the position of the fluorine group on the properties of the chromophores were investigated. These chromophores exhibit high decomposition temperatures whilst keeping molecular hyperpolarizabilities similar to those of the non-fluorinated analogues. The chromophore 2,4-diamino-4′-fluoro-3′-nitroazobenzene (2R-4F-3N-DIAMINE) shows a significant UV blue shift and a combination of good transparency, high thermal stability and nonlinearity in comparison with 2,4-diamino-2′-fluoro-5′-nitroazobenzene (2R-2F-5N-DIAMINE) and its non-fluorinated analogue 2,4-diamino-3′-nitroazobenzene (2R-3N-DIAMINE).

AB - The novel fluoronitroaryl azo diaminobenzene chromophores for potential NLO applications were synthesized and the effects of the position of the fluorine group on the properties of the chromophores were investigated. These chromophores exhibit high decomposition temperatures whilst keeping molecular hyperpolarizabilities similar to those of the non-fluorinated analogues. The chromophore 2,4-diamino-4′-fluoro-3′-nitroazobenzene (2R-4F-3N-DIAMINE) shows a significant UV blue shift and a combination of good transparency, high thermal stability and nonlinearity in comparison with 2,4-diamino-2′-fluoro-5′-nitroazobenzene (2R-2F-5N-DIAMINE) and its non-fluorinated analogue 2,4-diamino-3′-nitroazobenzene (2R-3N-DIAMINE).

KW - Chromophore

KW - Fluorine

KW - Hyperpolarizability

KW - Nonlinear optical materials

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U2 - 10.1016/j.tetlet.2005.01.022

DO - 10.1016/j.tetlet.2005.01.022

M3 - Article

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SN - 0040-4039

VL - 46

SP - 1511

EP - 1513

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 9

ER -

Synthesis and characterization of fluoronitroaryl azo diaminobenzene chromophores

Abstract

ASJC Scopus Subject Areas

Keywords

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