syntheses and properties of new photochromic diarylethene derivatives having a pyrazole unit

syntheses and properties of new photochromic diarylethene derivatives having a pyrazole unit

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1、TetrahedronLetters47(2006)6473–6477SynthesesandpropertiesofnewphotochromicdiarylethenederivativeshavingapyrazoleunitShouzhiPu,*TiansheYang,JingkunXuandBingChenJiangxiKeyLabofOrganicChemistry,JiangxiScienceandTechnologyNormalUniversity,Nanchang330013,PRChinaReceived30March

2、2006;revised3June2006;accepted6June2006Abstract—Newphotochromicdiarylethenes1a,2aand3abearingapyrazoleunithavebeensynthesized.Theirproperties,includingphotochromicreactivity,fluorescenceandelectrochemicalpropertieswereinvestigated.Thesecompoundsshowedgoodphotochro-micprope

3、rties,highcycloreversionquantumyieldandrelativelystrongfluorescence.Thecycloreversionquantumyieldsof1a,2aand3aare0.46,0.53and0.57,respectively,whicharelargerthanthoseoftheircyclizationquantumyields(0.43,0.45and0.47,respectively).Theoxidationsofdiarylethenes1a,2aand3awerein

4、itiatedat0.73,1.11and0.79V,respectively.Moreover,theposi-tionofthemethoxylsubstituenthadremarkableimpactsontheaboveopticalandelectrochemicalproperties.Ó2006PublishedbyElsevierLtd.Thedesignandsynthesisofphotochromiccompoundsarethermallyunstableandreturntotheopen-ringiso-is

5、anareaofintenseresearchbecauseoftheirwide-merseveninthedark.24Whenthearylgroupshavespreadpotentialapplicationinphotonicdevicessuchlowaromaticstabilizationenergy,thederivativesunder-ashigh-densityopticalrecordingmaterialsandphoto-gothermallyirreversiblephotochromicreaction

6、s.27Pyr-switches.1–6Amongvarioustypesofphotochromicazoleisanattractivearylunitbecauseofitslowcompounds,photochromicdiarylethenederivativeswitharomaticstabilizationenergyandthestructureissimilarheterocyclicarylringsarethemostpromisingorganictoisothiazole,expectingtoundergo

7、thermallyirrevers-photochromiccompoundsforphotoelectronicapplica-iblephotochromicreactions.Untilnow,photochromictionsbecauseoftheexcellentthermalstabilityofbothhybriddiarylethenederivativeswithpyrazoleandthio-ofthetwoisomers,fatigueresistantcharacter,rapidphenemoietieshav

8、enotyetbeenreported.responseandhighreactivityinsolidstate.7–10Inthepresentwork,wehavesynthesized

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