Synthesis of functionalised fluorescent dyes and their coupling to amines and amino acids

M.S.J. Briggs; I. Bruce; A.C. Simmonds; J.N. Miller; C.J. Moody; E. Swann

Synthesis of functionalised fluorescent dyes and their coupling to amines and amino acids

M.S.J. Briggs, I. Bruce, A.C. Simmonds, J.N. Miller, C.J. Moody, E. Swann

Life and Environmental Sciences

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

67 Citations (Scopus)

Abstract

A series of novel functionalised benzophenoxazinones, analogues of Nile Red, is prepared and their fluorescence properties evaluated. The ring system is prepared by reaction of 5-diethylamino-2-nitrosophenol with 1,6-dihydroxynaphthalene followed by alkylation of the 2-hydroxy group with 6-bromohexanoic acid derivatives. Subsequent ester cleavage under a variety of conditions gives the acid 6. Replacement of the 9-diethylamino group with the N-ethyl-(3-sulfonylpropyl)amino group is carried out to increase water solubility and the resulting dye 14 has similar fluorescence properties. The acid 6 is coupled to a range of amino compounds.

Original language	English
Pages (from-to)	1051-1058
Number of pages	8
Journal	Royal Chemical Society. Journal. Perkin Transactions 1
Issue number	7
Publication status	Published - 7 Apr 1997

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abstract = "A series of novel functionalised benzophenoxazinones, analogues of Nile Red, is prepared and their fluorescence properties evaluated. The ring system is prepared by reaction of 5-diethylamino-2-nitrosophenol with 1,6-dihydroxynaphthalene followed by alkylation of the 2-hydroxy group with 6-bromohexanoic acid derivatives. Subsequent ester cleavage under a variety of conditions gives the acid 6. Replacement of the 9-diethylamino group with the N-ethyl-(3-sulfonylpropyl)amino group is carried out to increase water solubility and the resulting dye 14 has similar fluorescence properties. The acid 6 is coupled to a range of amino compounds.",

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T1 - Synthesis of functionalised fluorescent dyes and their coupling to amines and amino acids

AU - Briggs, M.S.J.

AU - Bruce, I.

AU - Simmonds, A.C.

AU - Miller, J.N.

AU - Moody, C.J.

AU - Swann, E.

PY - 1997/4/7

Y1 - 1997/4/7

N2 - A series of novel functionalised benzophenoxazinones, analogues of Nile Red, is prepared and their fluorescence properties evaluated. The ring system is prepared by reaction of 5-diethylamino-2-nitrosophenol with 1,6-dihydroxynaphthalene followed by alkylation of the 2-hydroxy group with 6-bromohexanoic acid derivatives. Subsequent ester cleavage under a variety of conditions gives the acid 6. Replacement of the 9-diethylamino group with the N-ethyl-(3-sulfonylpropyl)amino group is carried out to increase water solubility and the resulting dye 14 has similar fluorescence properties. The acid 6 is coupled to a range of amino compounds.

AB - A series of novel functionalised benzophenoxazinones, analogues of Nile Red, is prepared and their fluorescence properties evaluated. The ring system is prepared by reaction of 5-diethylamino-2-nitrosophenol with 1,6-dihydroxynaphthalene followed by alkylation of the 2-hydroxy group with 6-bromohexanoic acid derivatives. Subsequent ester cleavage under a variety of conditions gives the acid 6. Replacement of the 9-diethylamino group with the N-ethyl-(3-sulfonylpropyl)amino group is carried out to increase water solubility and the resulting dye 14 has similar fluorescence properties. The acid 6 is coupled to a range of amino compounds.

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JO - Royal Chemical Society. Journal. Perkin Transactions 1

JF - Royal Chemical Society. Journal. Perkin Transactions 1

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Synthesis of functionalised fluorescent dyes and their coupling to amines and amino acids

Abstract

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