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Study On The Synthesis And Properties Of Dual-core Fe-S Clusters Containing Fluorogens

Posted on:2014-01-03Degree:MasterType:Thesis
Country:ChinaCandidate:J LiuFull Text:PDF
GTID:2231330395999770Subject:Fine chemicals
Abstract/Summary:PDF Full Text Request
Since1,8-naphthalene imide and anthracene are fluorescent chromophores with good performance, compounds containing these units have always been the research spot because of their good fluorescence properties and wide application in the life and scientific research. Their fluorescence properties might be changed by introducing metal atoms to the compounds. Fe-S clusters are widely found in the life, and they have a lot of potential applications in enzym-e simulation and catalytic synthesis of substances. This thesis describes the synthesis and fluor-escence properties of novel Fe-S clusters containing1,8-naphthalene imide and anthracene, what’s more, the fluorescence properties of Fe-S clusters containing1,8-naphthalene imide and anthracene treated with acids also have been studied. The detailed contents are as follows:(1) Six1,8-naphthalene imide derivatives[R-linker-COOH; R=1,8-naphthalene imide;2a, linker=CH2;2b, linker=(CH2)3;2c, linker=p-C6H4;R=4-bromine-1,8-naphthalene imide;2d, linker=CH2;2e, linker=p-C6H4, R=4-diethylamine-1,8-naphthalene imide;2f, linker=CH2] and three anthracene derivatives[R-linker-COOH; R=9-anthracene;4a, linker=;4b, linker=(CH)2;4c, linker=(CH2)2] were synthesized. The UV-Vis absorption spectra and emission spectra of compounds2a and4a in tetrahydrofuran were studied. The results indicate that the compounds2a and4a have showed good fluorescence properties in tetrahydrofuran.(2) Six novel compounds of Fe-S clusters containing1,8-naphthalene imide [Cp*Fe(μ-SEt)2(μ-O2C-linker-R) FeCp*][PF6][Cp*=η5-C5Me5; R=1,8-naphthalene imide;3a, linker=CH2;3b, linker=(CH2)3;3c, linker=p-C6H4; R=4-bromine-1,8-naphthalene imide;3d, linker=CH2;3e, linker=p-C6H4;;R=4-diethylamine-1,8-naphthalene imide;3f, linker=CH2] and three novel compounds of Fe-S clusters containing anthracene [Cp*Fe(μ-SEt)2(μ-O2C-linker-R) FeCp*][PF6][Cp*=η5-C5Me5; R=9-anthracene;5a, linker=;5b, linker=(CH)2;5c, linker=(CH2)2] were synthesized. The solid state structures of3c and5a were further determined by X-ray diffraction analysis. The UV-Vis absorption spectra and emission spectra of compound3a and5a in tetrahydrofuran were studied. The results indicate that the compounds3a and5a have showed no fluorescence properties in tetrahydrofuran.It shows that the introduction of Fe-S clusters leads to quenching the fluorescence properties. (3) Fluorescence properties of compounds3a-3f and5a-5c treated with acids were studied. The results indicate compounds5a treated with hydrochloric acid, acetic acid and trifluoroacetic acid in different time can increase the emission intensity greatly under the excitation of light whose wavelength is365nm, and the reaction process is reversible, other compounds treated with acids have no fluorescence emission.
Keywords/Search Tags:1,8-naphthalene imide, anthracene, Fe-S clusters, acid, fluorescence
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