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Title: Synthesis and physical properties of four hexazapentacene derivatives
Authors: Li, Gang
Wu, Yuechao
Gao, Junkuo
Wang, Chengyuan
Li, Junbo
Zhang, Huacheng
Zhao, Yang
Zhao, Yanli
Zhang, Qichun
Issue Date: 2012
Source: Li, G., Wu, Y., Gao, J., Wang, C., Li, J., Zhang, H., et al. (2012). Synthesis and physical properties of four hexazapentacene derivatives. Journal of The American Chemical Society, 134(50), 20298-20301.
Series/Report no.: Journal of the American chemical society
Abstract: In two steps from commercially available starting materials, four novel hexazapentacene derivatives have been synthesized through cyclocondensation reaction between tetraamines and 1,2-diketones. The observed optical bandgaps for 2,3,9,10-tetramethyl-1,4,6,8,11,13-hexaza-pentacene (TMHAP, 1), tetraethyl-1,4,6,8,11,13-hexaza-pentacene (TEHAP, 2), 1,2,3,4,10,11,12,13-octahydro-5,7, 9,14,16,18-hexazaheptacene (OHHAH, 3), and tetra(2-thioyl)-1,4,6,8,11,13-hexazapentacene (TTHAP, 4) are 2.55, 2.55, 2.45, and 2.25 eV, respectively. The cyclic voltammetry measurements show that all compounds exhibit one revisable reduction waves. The calculated bandgaps through DFT calculations for TMHAP (1), TEHAP (2), OHAH (3), and TTHAP (4) are 2.41, 2.41, 2.34, and 2.15 eV, respectivly, which are close to the experimental results. Our success in synthesizing hexazapentacene derivatives might offer a promising strategy to challenge larger azaacenes with more N atoms.
DOI: 10.1021/ja310131k
Rights: © 2012 American Chemical Society.
Fulltext Permission: none
Fulltext Availability: No Fulltext
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