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Title of article :
Synthesis and photophysical properties of N,N′-bis(4-cyanophenyl)-3,4,9,10-perylenebis(dicarboximide) and N,N′-bis(4-cyanophenyl)-1,4,5,8-naphthalenediimide
Author/Authors :
Uzun، نويسنده , , Duygu and Ozser، نويسنده , , Mustafa E and Yuney، نويسنده , , Kivanc and Icil، نويسنده , , Huriye and Demuth، نويسنده , , Martin، نويسنده ,
Issue Information :
روزنامه با شماره پیاپی سال 2003
Pages :
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Abstract :
N,N′-Bis(4-cyanophenyl)-1,4,5,8-naphthalenediimide (CN-NDI) and N,N′-bis(4-cyanophenyl)-3,4,9,10-perylenebis(dicarboximide) (CN-PDI) have been synthesized under special conditions in high yield. The compounds are characterized by UV-Vis, IR, NMR, MS, DSC, TGA and CV measurements. The fluorescence lifetimes, quantum yields and singlet-state energies are presented. CN groups at the phenyl moieties improve the thermal stability of the compounds. The LUMO energy values, −3.91 eV (CN-NDI in solution) and −3.96 eV (CN-NDI and CN-PDI at solid state), are determined by cyclic voltammetry. Whereas CN-NDI shows two reversible (−0.89 and −1.34 V) reduction steps (vs. Fc) in solution, CN-NDI and CN-PDI exhibit only one reversible wave at −0.48 V vs. Ag/AgCl at solid state, assigned to the one-electron reduction. Formation of aggregates shifts the UV absorption spectrum of CN-PDI to shorter wavelengths and its lifetime is measured as 4.6 ns at 580 nm. CN-PDI may be a promising dye for organic solar cells.
Keywords :
N , N?-Bis(4-cyanophenyl)-3 , 4 , 10-perylenebis(dicarboximide) , 9 , N , N?-Bis(4-cyanophenyl)-1 , 5 , 8-naphthalenediimide , Aggregation , electron transfer reactions , Organic solar cells , 4
Journal title :
Journal of Photochemistry and Photobiology:A:Chemistry
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