Synthesis and photophysical properties of iron-carbonyl complex-coumarin conjugates as potential bimodal IR-fluorescent probes

Paulina C. Glowacka; Nicolas Maindron; G. Richard Stephenson; Anthony Romieu; Pierre-Yves Renard; Flavio da Silva Emery

doi:10.1016/j.tetlet.2016.09.091

Synthesis and photophysical properties of iron-carbonyl complex-coumarin conjugates as potential bimodal IR-fluorescent probes

Paulina C. Glowacka, Nicolas Maindron, G. Richard Stephenson, Anthony Romieu, Pierre-Yves Renard, Flavio da Silva Emery

Chemistry of Materials and Catalysis

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

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Abstract

An expedient synthesis of the first examples of iron-carbonyl complex-coumarin conjugates is reported. 7-Amino/7-hydroxycoumarin derivatives have been readily derivatized through an easily implemented single-step reaction involving the tricarbonyl(η5-cyclohexadienyl)iron(1+) cation [(C6H7)Fe(CO)3]+. The scope and limitations of this N-/O-alkylation reaction were also investigated. The fluorescence properties of these novel metal-carbonyl complexes have been studied and support their further use as valuable building blocks in the design of bimodal contrast agents for combined vibrational and fluorescence imaging.

Original language	English
Pages (from-to)	4991–4996
Number of pages	6
Journal	Tetrahedron Letters
Volume	57
Issue number	45
Early online date	28 Sep 2016
DOIs	https://doi.org/10.1016/j.tetlet.2016.09.091
Publication status	Published - 9 Nov 2016

Keywords

Coumarins
Dual imaging probes
Fluorescence
Infrared
Iron-carbonyl complexes

Access to Document

10.1016/j.tetlet.2016.09.091

Accepted manuscriptAccepted author manuscript, 782 KBLicence: CC BY-NC-ND

http://linkinghub.elsevier.com/retrieve/pii/S0040403916312849

Cite this

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title = "Synthesis and photophysical properties of iron-carbonyl complex-coumarin conjugates as potential bimodal IR-fluorescent probes",

abstract = "An expedient synthesis of the first examples of iron-carbonyl complex-coumarin conjugates is reported. 7-Amino/7-hydroxycoumarin derivatives have been readily derivatized through an easily implemented single-step reaction involving the tricarbonyl(η5-cyclohexadienyl)iron(1+) cation [(C6H7)Fe(CO)3]+. The scope and limitations of this N-/O-alkylation reaction were also investigated. The fluorescence properties of these novel metal-carbonyl complexes have been studied and support their further use as valuable building blocks in the design of bimodal contrast agents for combined vibrational and fluorescence imaging.",

keywords = "Coumarins, Dual imaging probes, Fluorescence, Infrared, Iron-carbonyl complexes",

author = "Glowacka, {Paulina C.} and Nicolas Maindron and Stephenson, {G. Richard} and Anthony Romieu and Pierre-Yves Renard and Emery, {Flavio da Silva}",

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doi = "10.1016/j.tetlet.2016.09.091",

language = "English",

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journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Synthesis and photophysical properties of iron-carbonyl complex-coumarin conjugates as potential bimodal IR-fluorescent probes

AU - Glowacka, Paulina C.

AU - Maindron, Nicolas

AU - Stephenson, G. Richard

AU - Romieu, Anthony

AU - Renard, Pierre-Yves

AU - Emery, Flavio da Silva

PY - 2016/11/9

Y1 - 2016/11/9

N2 - An expedient synthesis of the first examples of iron-carbonyl complex-coumarin conjugates is reported. 7-Amino/7-hydroxycoumarin derivatives have been readily derivatized through an easily implemented single-step reaction involving the tricarbonyl(η5-cyclohexadienyl)iron(1+) cation [(C6H7)Fe(CO)3]+. The scope and limitations of this N-/O-alkylation reaction were also investigated. The fluorescence properties of these novel metal-carbonyl complexes have been studied and support their further use as valuable building blocks in the design of bimodal contrast agents for combined vibrational and fluorescence imaging.

AB - An expedient synthesis of the first examples of iron-carbonyl complex-coumarin conjugates is reported. 7-Amino/7-hydroxycoumarin derivatives have been readily derivatized through an easily implemented single-step reaction involving the tricarbonyl(η5-cyclohexadienyl)iron(1+) cation [(C6H7)Fe(CO)3]+. The scope and limitations of this N-/O-alkylation reaction were also investigated. The fluorescence properties of these novel metal-carbonyl complexes have been studied and support their further use as valuable building blocks in the design of bimodal contrast agents for combined vibrational and fluorescence imaging.

KW - Coumarins

KW - Dual imaging probes

KW - Fluorescence

KW - Infrared

KW - Iron-carbonyl complexes

U2 - 10.1016/j.tetlet.2016.09.091

DO - 10.1016/j.tetlet.2016.09.091

M3 - Article

VL - 57

SP - 4991

EP - 4996

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 45

ER -