| Since Eric Clar firstly proposed the concept of“acene”in 1939,the acene-based materials,especially their star molecules such as tetracene and pentacene,have been widely used as activated layers in organic field effect transistor?OFET?,organic light-emitting diode?OLED?,organic solar cells?OPV?and other organic electronics.Actually,acene is a kind of typical p-type semiconductor,while the development n-type semiconductors is largerly lag behind the p-type semiconductors,thus developing n-type semiconductors with simple synthetic process,high stability is highly desirable.Inserting heteroatoms into the skeleton of acenes may change the charge transport type of acenes.Researches showed that the insertion of N atoms could adjust the charge transport propeties of acenes from p-type to bipolar or n-type.Nowadays,most of the reported results were focused on the pyrazine-ring containing azaacenes,other N-heterocycle-containing azaacenes were rarely reported.This thesis firstly reviewed the recent progress in the field of azaacene including the synthetic methods and applications,and then three kinds of novel azaacenes were introduced,the research contents are as follows:The twisttetraacene L1 and its full-carbon derivative L2 had been synthesized and fully characterized.Studies showed that the fluorescence of L2 was not changed after the addition of picric acid?PA?,while the fluroescence of L1 was changed largerly when the addtion of PA.Upon the addition of PA,the maximum emission wavelength of L1 was red-shifted from 447 nm to 555 nm,the intensity of fluorescence reduced nearly 120 times.Meanwhile,othe nitro-containing compounds showed no interferences especillay p-nitrophenol and 2,4-dinitrophenol exhibited weak fluroencence quenching.The calculated detection limition reached 2.6×10-6 M.Obviously,the insertion of pyridine ring into the sketeton of twistacene largely enhanced the selectivity and sensitivity for picric acid.Considering the large steric hidrance of TIPS group,the o-naphthalenediamine derivative with two TIPS groups had been condesation with hexaketocyclohexane to construct the precursor of tetraazaheptacene?HTAHD?,and efforts were focused the construction of tetraazaheptacene.The optical and electrochemical properties of HTAHD and TAHD had been fully investigated.Moreover,photoelectrochemical behaviors confirmed the n-type semiconductor of TAHD,and TAHD exhibited a negative photovoltage and recyclable photocurrent responses.Tetraphenylphthalic-based materials have been widely used to construct organic solid state emission materials since this kind of structures can avoid the aggregation induced quenching effect.Here,compounds M2 and M3?isomers?had been obtained through one step condensation between tetraphenylphthalic anhydrid and benzene-1,2,4,5-tetraamine,the one-side product?M1?had also been obtained for comparision.Studies showed that the fluorescence quantum efficency of M2 and M3are higher the that of M1,while the fluorescence quantum efficency of M2 is nearly 3multiple higher than M3.Moreover,OLED test confirmed M2 shows a greater twice the luminance than M3 in the same current density,The maximum current efficiencyof M2 is 7.8 cd/A,The maximum current efficiency of M3 is 3.6 cd/A. |
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