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Metalloporphyrazines annulated with tetrathiafulvalene: synthesis, photophysical and electrochemical properties
Leng Fengshou 1,Zheng Ningjuan 2,Chen Tie 2,Kan Yuhe 3,Yin Bingzhu 2 * #
1.Key Laboratory of Natural Resources of Changbai Mountain & Functional Molecules of the Ministry of Education, Department of Chemistry, Yanbian University, Yanji 133002, P. R. China
2.Key Laboratory of Natural Resources of Changbai Mountain & Functional Molecules of the Ministry of Education, Department of Chemistry, Yanbian University, Yanji 133002, P. R. China
3.Jiangsu Province Key Laboratory for Chemistry of Low-Dimensional Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huaian 223300
*Correspondence author
#Submitted by
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Funding: National Natural Science Foundation of China （No.grant No.21062022), Specialized Research Fund for the Doctoral Program of Higher Education）
Opened online:14 January 2014
Accepted by: none
Citation: Leng Fengshou,Zheng Ningjuan,Chen Tie.Metalloporphyrazines annulated with tetrathiafulvalene: synthesis, photophysical and electrochemical properties[OL]. [14 January 2014] http://en.paper.edu.cn/en_releasepaper/content/4581014
 
 
A series of metalloporphyrazines annulated with tetrathiafulvalenes, bearing eight electron-withdrawing alkoxy-carbonyl groups at the periphery, were synthesized via the cyclotetramerization of dialkyl 6,7-dicyanotetrathiafulvalene-2,3-dicarboxylate in the presence of corresponding metal salts in alkanol. All newly synthesized compounds showed typical electronic spectra of the metallo-porphyrazines, consisting of a strong and broad Q-band and a strong and sharp B-band. A theoretical study rationalized the transition nature for the Q-band absorption and supported the proposed intramolecular charge transfer interactions. From cyclic voltammetry, the energy levels values of HOMO and LUMO were estimated to be -5.03 to -5.30 eV and -3.50 to -3.60 eV, respectively, which satisfy the conditions required for the semiconductors used in the air-operable devices. The selected compunds (5a, 5c-5d) were efficiently incorporated into an organogel made of (1R, 2R)-trans-1,2-bis(dodecanoyl-amino)cyclohexane by means of multiple cooperative non-covalent interactions, and SEM revealed the formation of unique sheet-like nanostructures.
Keywords:Tetrathiafulvalene, Metalloporphyrazine, Photophysical property, Electrochemical property, Theoretical study
 
 
 

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