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Updated: May 16, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Synthesis and physical properties of four hexazapentacene derivatives
Gang Li1, Yuechao Wu, Junkuo Gao
1School of Materials Science and Engineering, Nanyang Technological University, Singapore 639798, Singapore.
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.
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