TY - JOUR
T1 - Fast and inexpensive synthesis of pentacene with high yield using 6,13-pentacenequinone as precursor
AU - Mota, María L.
AU - Rodriguez, Bibiana
AU - Carrillo, Amanda
AU - Ambrosio, Roberto C.
AU - Luque, Priscy A.
AU - Mireles, Marcela
AU - Vivaldo, Israel
AU - Quevedo, Manuel A.
N1 - Publisher Copyright:
© 2017 Elsevier B.V.
PY - 2018/2/15
Y1 - 2018/2/15
N2 - Pentacene is an important semiconductor in the field of organic electronics. In this work is presented an alternative synthesis procedure to obtain pentacene from 6,13-pentacenequinone as a precursor. Synthesis of pentacene was performed in two reactions, Diels-Adler cycloaddition of 6,13-pentacenequinone followed by 6,13-pentacenequinone reduction to pentacene, employing LiAlH4 as reducing agent. The products were characterized by Fourier Transform Infrared Spectroscopy (FTIR), 1H-Nuclear Magnetic Resonance Spectroscopy (1H-NMR), X-Ray Diffraction (XRD), Thermogravimetric Analysis (TGA) and Ultraviolet–Visible Spectroscopy (UV-VIS). In this work, 6,13-pentacenequinone was synthetized with a high yield (55%) using an alternative method. The optimization process resulted in an overall reduction of reaction time while exhibiting high yield. The method presented here provides an affordable pentacene synthesis route with high purity, which can be further applied for research and development of organic electronic applications.
AB - Pentacene is an important semiconductor in the field of organic electronics. In this work is presented an alternative synthesis procedure to obtain pentacene from 6,13-pentacenequinone as a precursor. Synthesis of pentacene was performed in two reactions, Diels-Adler cycloaddition of 6,13-pentacenequinone followed by 6,13-pentacenequinone reduction to pentacene, employing LiAlH4 as reducing agent. The products were characterized by Fourier Transform Infrared Spectroscopy (FTIR), 1H-Nuclear Magnetic Resonance Spectroscopy (1H-NMR), X-Ray Diffraction (XRD), Thermogravimetric Analysis (TGA) and Ultraviolet–Visible Spectroscopy (UV-VIS). In this work, 6,13-pentacenequinone was synthetized with a high yield (55%) using an alternative method. The optimization process resulted in an overall reduction of reaction time while exhibiting high yield. The method presented here provides an affordable pentacene synthesis route with high purity, which can be further applied for research and development of organic electronic applications.
KW - Organic synthesis
KW - Pentacene
KW - Semiconductor
UR - http://www.scopus.com/inward/record.url?scp=85032373323&partnerID=8YFLogxK
U2 - 10.1016/j.molstruc.2017.10.070
DO - 10.1016/j.molstruc.2017.10.070
M3 - Artículo
AN - SCOPUS:85032373323
SN - 0022-2860
VL - 1154
SP - 511
EP - 515
JO - Journal of Molecular Structure
JF - Journal of Molecular Structure
ER -