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. 2022 Jul 6;27(14):4340.
doi: 10.3390/molecules27144340.

Microwave Irradiation as a Powerful Tool for the Preparation of n-Type Benzotriazole Semiconductors with Applications in Organic Field-Effect Transistors

Iván Torres-Moya  1 , Alexandra Harbuzaru  2 , Beatriz Donoso  1 , Pilar Prieto  1 , Rocío Ponce Ortiz  2 , Ángel Díaz-Ortiz  1
Affiliations

Microwave Irradiation as a Powerful Tool for the Preparation of n-Type Benzotriazole Semiconductors with Applications in Organic Field-Effect Transistors

Iván Torres-Moya et al. Molecules. .

Abstract

In this work, as an equivocal proof of the potential of microwave irradiation in organic synthesis, a complex pyrazine-decorated benzotriazole derivative that is challenging to prepare under conventional conditions has been obtained upon microwave irradiation, thus efficiently improving the process and yields, dramatically decreasing the reaction times and resulting in an environmentally friendly synthetic procedure. In addition, this useful derivative could be applied in organic electronics, specifically in organic field-effect transistors (OFETs), exhibiting the highest electron mobilities reported to date for benzotriazole discrete molecules, of around 10-2 cm2V-1s-1.

Keywords: OFETs; benzotriazole; microwave irradiation.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
(a) General structure of the benzotriazole-based multidonor–acceptor system described in this work. (b) D-A-D benzotriazole derivatives previously reported by our research group [45].
Figure 2
Figure 2
Optimized structure and frontier molecular orbitals corresponding to derivative 1, calculated at the B3LYP/6-31G (d,p) level of theory.
Scheme 1
Scheme 1
Synthetic route for the multidonor–acceptor benzotriazole derivative 1.
Scheme 2
Scheme 2
Synthetic procedure for alkynyl derivative 12.
Figure 3
Figure 3
UV–Visible absorption (a) and emission (b) spectra of compound 1 (298 K, DMSO, 1 × 10−5 M).
Figure 4
Figure 4
Output (a) and transfer (b) plots registered for 1 at positive bias. VG varies from −20 to 100 V (in 20 V steps).
Figure 5
Figure 5
XRD pattern of benzotriazole 1 thin films prepared under the optimal device fabrication conditions.
See this image and copyright information in PMC

References

    1. Gedye R., Smith F., Westaway K., Ali H., Baldisera L., Laberge L., Rousell J. The use of microwave ovens for rapid organic synthesis. Tetrahedron Lett. 1986;27:279–282. doi: 10.1016/S0040-4039(00)83996-9. - DOI
    1. Giguere R.J., Bray T.L., Duncan S.M., Majetich G. Application of commercial microwave ovens to organic synthesis. Tetrahedron Lett. 1986;27:4945–4948. doi: 10.1016/S0040-4039(00)85103-5. - DOI
    1. De la Hoz A., Loypy A. Microwaves in Organic Synthesis. Wiley-VCH; Weinheim, Germany: 2012.
    1. Sanhi R., Singh V. Green Chemistry for Environmental Remediation. Wiley; Hoboken, NJ, USA: 2012.
    1. Pollastri M.P., Devine W.G. Microwave Synthesis in Green Techniques for Organic Synthesis and Medicinal Chemistry. Wiley; Chichester, UK: 2012.

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