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Study On The Conformational Control Of Tetraphenylethene Derivatives

Posted on:2020-11-14Degree:MasterType:Thesis
Country:ChinaCandidate:X C LuFull Text:PDF
GTID:2381330572471526Subject:Medicinal chemistry
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Tetraphenylene,as a kind of organic fluorescent materials,has its unique properties.Different from the aggregation-caused quenching effect that conventional fluorescent molecules normally suffer in their aggregated or the solid state,tetraphenylene becomes highly luminescent in the aggreated state.The propeller-like conformation makes TPE chiral,resulting two enantiomeric forms P-conformer and M-conformer,differ in the sense of helicity.The rotational barriers are very low that TPE does not possess optical activity in solution.There are few reports about the successful synthesis of tetraphenylenes with single chirality.We plan to use the group with definite spatial orientation to control the rotation direction of tetraphenylene.In the second part,two novel tetraphenylenes derivative R-BINOL-TPE and S-BINOL-TPE,were designed and prepared.The tetraphenylene is bridged between its two phenyl rings by short tethers stretched out by dinaphthol.Through the above-mentioned approach,the rotation direction of four phenyl rings in tetraphenylene can be controlled.In the crystal of R-BINOL-TPE,all the tetraphenylene is fixed as M-conformer while the S-BINOL-TPE is fixed as P-conformer.Here,we reported that R-BINOL-M-TPE and S-BINOL-P-TPE are the most typical and the most studied AIE compound,and showed a strong Cotton effect in CD spectrum.Unfortunately,in the further CPL spectrum investigations,no obvious CPL singals were found.This may be related to the fact that when we "bind"the phenyl rings,only two of them were limited.And the other two phenyl rings can still rotate freely.In the third part,a novel tetraphenylenes derivative 2Py-TPE,were designed and prepared.Two pyrene rings are replaced the phenyl rings in the tetraphenylenes.2Py-TPE is the typical AIE molecule.In the single-crystal structures of 2Py-TPE,molecules are tightly bound by pyrene ring ?-? conjugation.And there is a long J-aggration in it.The properties of this compound need to be further determined.
Keywords/Search Tags:tetraphenylene, binaphthol, AIE, chiral, pyrene
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