Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/153443
Title: Synthesis of 5-azatetracene and comparison of its optical and electrochemical properties with tetracene
Authors: Ghosh, Animesh
Budanovic, Maja
Li, Tianjiao
Liang, Caihong
Klein, Maciej
Soci, Cesare
Webster, Richard David
Gurzadyan, Gagik G.
Grimsdale, Andrew C.
Keywords: Science::Chemistry::Organic chemistry
Issue Date: 2021
Source: Ghosh, A., Budanovic, M., Li, T., Liang, C., Klein, M., Soci, C., Webster, R. D., Gurzadyan, G. G. & Grimsdale, A. C. (2021). Synthesis of 5-azatetracene and comparison of its optical and electrochemical properties with tetracene. Asian Journal of Oragnic Chemistry, 10(10), 2571-2579. https://dx.doi.org/10.1002/ajoc.202100373
Project: AcRF Tier 1 RG117/15 
AcRF Tier 2 MOE2019-T2-1-085 
Journal: Asian Journal of Oragnic Chemistry 
Abstract: A four-step route for the synthesis of 5-azatetraceene (benzo[b]acridine) has been developed, employing a base-catalysed Friedlander condensation reaction between 3-amino-2-napthaldehyde and cyclohexanone as the key step followed by dehydrogenation of the intermediate. The optical and electrochemical properties of the 5-azatetracene were investigated by UV-vis and photoluminescence spectroscopy, and by cyclic voltammetry and compared with those of tetracene. It is found that 5-azatetracene shows broader absorption in the visible region than tetracene, exhibits a higher luminescence quantum efficiency, and possesses a lower-lying LUMO level and smaller HOMO-LUMO band gap. Time-resolved PL spectroscopy was used to elucidate the reasons for the more efficient luminescence of 5-azatetracene. Field-effect transistor measurements revealed the ambipolar nature of charge transport in 5-azatetracene.
URI: https://hdl.handle.net/10356/153443
ISSN: 2193-5807
DOI: 10.1002/ajoc.202100373
Rights: This is the peer reviewed version of the following article: Ghosh, A., Budanovic, M., Li, T., Liang, C., Klein, M., Soci, C., Webster, R. D., Gurzadyan, G. G. & Grimsdale, A. C. (2021). Synthesis of 5-azatetracene and comparison of its optical and electrochemical properties with tetracene. Asian Journal of Oragnic Chemistry, 10(10), 2571-2579, which has been published in final form at https://doi.org/10.1002/ajoc.202100373. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
Fulltext Permission: embargo_20221107
Fulltext Availability: With Fulltext
Appears in Collections:ERI@N Journal Articles
MSE Journal Articles
SPMS Journal Articles

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Azatetracene Manuscript accepted article.pdf
  Until 2022-11-07
765.72 kBAdobe PDFUnder embargo until Nov 07, 2022
Supporting Information azatetracene accepted paper.pdf
  Until 2022-11-07
1.22 MBAdobe PDFUnder embargo until Nov 07, 2022

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