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Synthesis And Properties Of Indolocarbazole-based Organogelators And Diketone-boron Difluoride-based Fluorencent Probe Molecules

Posted on:2014-02-27Degree:MasterType:Thesis
Country:ChinaCandidate:H J ZhangFull Text:PDF
GTID:2231330395497573Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
Recently, great attention has been paid to organic functional materials. Becausecarbazole and diketone boron units are typical moieties for constructing variousfunctional materials, we designed and synthesized three indolocarbazole derivatives.Their self-assembling properties were investigated. Moreover, a diketone difluoridederivative containing trifluoroacetyl unit was synthesized and its responsive behaviorsfor anions was measured. The obtained results are as follows:(1) Three N-hexadecyl indolocarbazole derivatives were synthesized. It wasfound that the bend-shaped indolo[2,3-b]carbazole derivative could form gels in manykinds of organic solvents because of the balanced π-π interaction between molecules.Indolo[3,2-b]carbazole derivative with rod-like-skeleton showed poor gelationability due to strong π-π interaction. Furthermore, a bend-shapedindolo[2,3-c]carbazole derivative could not form gel in the tested solvents owing toweaker π-π interaction.(2) A-diketone-boron difluorides derivative with trifluoroacetyl group wassynthesized, and its responsive behaviors for anions were studied. The obtainedresults suggested that this sensor could selectively respond AcO–, F–and H2PO4-–because trifluoromethyl unit increase the acidity of NH and then the deprotonation ofNH happened upon the addition of anions. Its solution exhibits visual color andfluorescence changes upon addition of AcO–, F–and H2PO4-–. No significant colorchange was observed upon addition of other anions such as chloride, bromide, iodide,and hydrogen sulfate. The binding constants showed the binding order: AcO> F>H2PO4-.
Keywords/Search Tags:-gel, π-π interaction, β-diketone boron, fluorescent sensing, anion
PDF Full Text Request
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