Journal
ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 10, Issue 10, Pages 2571-2579Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202100373
Keywords
cyclic voltammetry; field-effect transistor; Friedlander condensation; nitrogen heterocycles; photoluminescence spectroscopy; time resolved measurements
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Funding
- Singapore Ministry of Education [RG117/15, MOE2019-T2-1-085]
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A four-step synthesis route for 5-azatetracene was developed, showing advantages in absorption, luminescence, and energy levels compared to tetracene. Time-resolved PL spectroscopy and field-effect transistor measurements were used to investigate the luminescence mechanism and charge transport properties in more depth.
A four-step route for the synthesis of 5-azatetracene (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.
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