Synthesis and physical properties of four hexazapentacene derivatives
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), tetrae...
| Main Authors: | , , , , , , , , |
|---|---|
| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2013
|
| Online Access: | https://hdl.handle.net/10356/97604 http://hdl.handle.net/10220/11212 |
| _version_ | 1824454210459009024 |
|---|---|
| author | Li, Gang Wu, Yuechao Gao, Junkuo Wang, Chengyuan Li, Junbo Zhang, Huacheng Zhao, Yang Zhao, Yanli Zhang, Qichun |
| author2 | School of Materials Science & Engineering |
| author_facet | School of Materials Science & Engineering Li, Gang Wu, Yuechao Gao, Junkuo Wang, Chengyuan Li, Junbo Zhang, Huacheng Zhao, Yang Zhao, Yanli Zhang, Qichun |
| author_sort | Li, Gang |
| collection | NTU |
| description | 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. |
| first_indexed | 2025-02-19T03:18:41Z |
| format | Journal Article |
| id | ntu-10356/97604 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2025-02-19T03:18:41Z |
| publishDate | 2013 |
| record_format | dspace |
| spelling | ntu-10356/976042020-06-01T10:26:36Z Synthesis and physical properties of four hexazapentacene derivatives Li, Gang Wu, Yuechao Gao, Junkuo Wang, Chengyuan Li, Junbo Zhang, Huacheng Zhao, Yang Zhao, Yanli Zhang, Qichun School of Materials Science & Engineering 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. 2013-07-11T06:46:08Z 2019-12-06T19:44:30Z 2013-07-11T06:46:08Z 2019-12-06T19:44:30Z 2012 2012 Journal Article 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. https://hdl.handle.net/10356/97604 http://hdl.handle.net/10220/11212 10.1021/ja310131k en Journal of the American chemical society © 2012 American Chemical Society. |
| spellingShingle | Li, Gang Wu, Yuechao Gao, Junkuo Wang, Chengyuan Li, Junbo Zhang, Huacheng Zhao, Yang Zhao, Yanli Zhang, Qichun Synthesis and physical properties of four hexazapentacene derivatives |
| title | Synthesis and physical properties of four hexazapentacene derivatives |
| title_full | Synthesis and physical properties of four hexazapentacene derivatives |
| title_fullStr | Synthesis and physical properties of four hexazapentacene derivatives |
| title_full_unstemmed | Synthesis and physical properties of four hexazapentacene derivatives |
| title_short | Synthesis and physical properties of four hexazapentacene derivatives |
| title_sort | synthesis and physical properties of four hexazapentacene derivatives |
| url | https://hdl.handle.net/10356/97604 http://hdl.handle.net/10220/11212 |
| work_keys_str_mv | AT ligang synthesisandphysicalpropertiesoffourhexazapentacenederivatives AT wuyuechao synthesisandphysicalpropertiesoffourhexazapentacenederivatives AT gaojunkuo synthesisandphysicalpropertiesoffourhexazapentacenederivatives AT wangchengyuan synthesisandphysicalpropertiesoffourhexazapentacenederivatives AT lijunbo synthesisandphysicalpropertiesoffourhexazapentacenederivatives AT zhanghuacheng synthesisandphysicalpropertiesoffourhexazapentacenederivatives AT zhaoyang synthesisandphysicalpropertiesoffourhexazapentacenederivatives AT zhaoyanli synthesisandphysicalpropertiesoffourhexazapentacenederivatives AT zhangqichun synthesisandphysicalpropertiesoffourhexazapentacenederivatives |