syntheses and optoelectronic properties of four photochromic dithienylethenes

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1、Tetrahedron61(2005)66236629SynthesesandoptoelectronicpropertiesoffourphotochromicdithienylethenesShouzhiPu,*TiansheYang,JingkunXu,LiangShen,GuizhenLi,QiangXiaoandBingChenJiangxiKeyLabofOrganicChemistry,JiangxiScienceandTechnologyNormalUniversity,Nanchang330013,ChinaRece

2、ived6December2004;revised12April2005;accepted14April2005Availableonline23May2005AbstractFourphotochromicdithienylethenecompounds,1,2-bis(2-methyl-5-naphthalene-3-thienyl)perfluorocyclopentene1a,1,2-bis[2-methyl-5(p-fluorophenyl)-3-thienyl]perfluorocyclopentene2a,1,2-bis[2-

3、methyl-5(p-ethoxyphenyl)-3-thienyl]perfluorocyclopentene3a,and1,2-bis[2-methyl-5(p-N,N-dimethylaminophenyl)-3-thienyl]perfluorocyclopentene4aweresynthesized,andtheiroptoelectronicproperties,suchasphotochromisminsolutionaswellasinpoly-methylmethacrylate(PMMA)amorphousfilms,

4、fluorescencesandelectrochemicalpropertieswereinvestigatedindetail.ThesedithienyletheneshaveshowngoodphotochromicbehaviorbothinsolutionandinPMMAamorphousfilm.AllofthemexhibitedrelativelystrongfluorescenceandgaveabathochromicshiftuponincreasingconcentrationinTHF.Theirreversi

5、bleanodicoxidationof1a,2aand4awasobservedbyperformingcyclicvoltammetryexperiments.q2005ElsevierLtd.Allrightsreserved.5,23,241.Introductionrefractiveindices,etc.Themostimportantdifferenceisthatwhilethep-systemsoftwoarylringsareseparatedinOrganicphotochromicmaterialshavea

6、ttractedmuchtheopen-ringisomer,thep-conjugationisdelocalized,25attention,becauseoftheirpotentialapplicationtoopticalthroughoutthemoleculeintheclosed-ringisomer.Byfar,16manydithienylethenesderivativesandtheiroptoelectronicmemorymediaandopticalswitches.Amongvarious3,4,7pr

7、opertieswerereported.3,26,27Dithienylethenesbearingtypesofphotochromiccompounds,diarylethenederiva-4,8,9phenylgroupsontheendareofspecialinterest,becausethetives,bearingtwothiophene-derivedgroupsarethemostpromisingbecauseoftheirexcellentthermalstabilityendgroupcanbesubst

8、itutedbyelectrondonatinggrouporofbothisomers,3,1012fatigueresistantcharacter,13,14rapidelectronwithdrawinggrou