Syntheses And Properties Of Naphthacene And Benzonaphthosilole Derivatives

Among the numerous synthetic methods of naphthacene derivatives,the zirconium-induced synthesis method uses inexpensive alkynes as raw materials with mild reaction conditions and high yields and various groups can be selectively substituted on the aromatic ring.6,11-diphenyl-1,2,3,4-tetrapropyltetracene and2,3,6,11-tetrabutyltetracene are two molecules that have potential photoelectric properties,but related performance studies have not been reported.There is no report of aromatic ring derivatization of benzonaphthosilole.Therefore,it is of great significance to study the performance of the above two tetracene derivatives and the synthesis of benzonaphthosilole.In this paper,zirconium-induced synthesis method was used to synthesize the above two naphthacene derivatives,and their optoelectronic properties and stability were studied.Their UV-Vis absorption spectras,fluorescence spectras,cyclic voltammetry,TGA and DSC characteristics were tested.The test results show that the two derivatives have obvious absorption in the visible range,and their fluorescence is yellow and green.The optical energy gap is in the range of 2.3eV to 2.4eV,and the electrochemical energy gap is in the range of 2.5eV to 2.6eV,T_95%is greater than260°C,and melting temperature is greater than 130°C.The above test results indicate that the above naphthacene derivatives have certain application ability in organic photoelectric materials.In this paper,the quantum chemical calculations for the HOMO,LUMO,UV-Vis absorption spectra and fluorescence spectra of the above tetracene derivatives were carried out.The results show that the PBE0/6-31G*method is accurate in estimating the UV-Vis absorption spectrum of the naphthacene derivatives.The peak position of the wavelength of the fluorescence spectrum is accurate,and the error is Within 30nm.The B3LYP/6-31G*method has high-precision calculation results for the energy gap of the above tetracene derivatives,and the calculated value of the electrochemical energy gap is only about 0.16 eV higher than the measured value.It can be concluded that B3LYP functional is more appropriate when calculating the energy gap values of naphthacene and benzonaphthosilole derivatives,and PBE0 is appropriate when calculating the absorption and fluorescence spectra of the above substances.This article designed the synthetic route of benzonaphthosilole derivative according to the synthesis method of tetracene,and successfully synthesized benzonaphthyridene derivatives containing propyl,phenyl and methoxycarbonyl groups.It is the first report of the derivatization of benzonaphthosilole aromatic ring,which expands the application range of zirconium-induced reaction,promotes the synthesis of benzonaphthosilole derivatives.In this paper,the optimized calculation method is used to calculate the properties of the benzonaphthosilole derivative.The results show that the derivative is more suitable for the construction of molecules with larger conjugation systems.At the same time,we also found in the calculation process that the propyl and methoxycarbonyl groups have certain induction effects on the HOMO and LUMO distribution of the molecule.