Mechanism of hydride transfer reaction from 4-(dimethylamino)phenyl methane derivatives to 2,3-dichloro-5,6-dicyano-p-benzoquinone

Yamamoto, Shunzo; Sakurai, Takao; Liu, Yingjin; Sueishi, Yoshimi

doi:10.1039/a809358j

Cited by 23 publications

(26 citation statements)

References 9 publications

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“…As consequence, the electron back transfer from C 60 is no longer possible and a stable doping has been obtained. The same effect has been observed for stronger acceptors like DDQ or TCNQ where LCV is directly oxidized to CV by the hydride transfer without requiring illumination to reach an excited state as it is the case for weaker acceptors like C 60 70–72.…”

Section: Doping Fundamentalssupporting

confidence: 55%

Doping of organic semiconductors

Lüssem

Riede

Leo

2012

Physica Status Solidi (a)

552

542

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The understanding and applications of organic semiconductors have shown remarkable progress in recent years. This material class has been developed from being a lab curiosity to the basis of first successful products as small organic LED (OLED) displays; other areas of application such as OLED lighting and organic photovoltaics are on the verge of broad commercialization. Organic semiconductors are superior to inorganic ones for low‐cost and large‐area optoelectronics due to their flexibility, easy deposition, and broad variety, making tailor‐made materials possible. However, electrical doping of organic semiconductors, i.e. the controlled adjustment of Fermi level that has been extremely important to the success of inorganic semiconductors, is still in its infancy. This review will discuss recent work on both fundamental principles and applications of doping, focused primarily to doping of evaporated organic layers with molecular dopants. Recently, both p‐ and n‐type molecular dopants have been developed that lead to efficient and stable doping of organic thin films. Due to doping, the conductivity of the doped layers increases several orders of magnitude and allows for quasi‐Ohmic contacts between organic layers and metal electrodes. Besides reducing voltage losses, doping thus also gives design freedom in terms of transport layer thickness and electrode choice. The use of doping in applications like OLEDs and organic solar cells is highlighted in this review. Overall, controlled molecular doping can be considered as key enabling technology for many different organic device types that can lead to significant improvements in efficiencies and lifetimes.

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Section: Doping Fundamentalssupporting

confidence: 55%

Doping of organic semiconductors

Lüssem

Riede

Leo

2012

Physica Status Solidi (a)

552

542

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Section: N-type Doping Using Precursorssupporting

confidence: 55%

Doping of Organic Semiconductors

Lüssem

Riede

Leo

2012

Physics of Organic Semiconductors

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Björn Lü ssem studied electrical engineering at the Rheinisch-Westfälische Technische Hochschule (RWTH) in Aachen and the University of Bath and obtained his degree as Diplomingenieur in 2003. He prepared his PhD thesis at the Research Center in Jülich, Germany, in the field of molecular electronics. His thesis concentrates on scanning tunneling microscopy of pure and mixed selfassembled monolayers and has been awarded the VDE-Promotionspreis and the Günther-Leibfried-Preis. After staying at the Materials Science Laboratory of Sony in Stuttgart from 2006 to 2008, he joined Prof. Leo's group at the Technische Universität Dresden where he is now the head of the New Devices Group. His main interests are new semiconducting devices based on organic materials and their differences or similarities to inorganic semiconductors. Moritz Riede studied physics at the University of Cambridge, UK, where he received his MSc degree in 2002. He obtained his PhD degree from the University of Konstanz in 2006 for research carried out at the Fraunhofer-Institut für Solare Energiesysteme and the Freiburger Materialforschungszentrum FMF. The focus of his thesis was on solution-processed organic solar cells. After his PhD he joined the research group of Prof. Leo at the Institut für Angewandte Photophysik (IAPP) of the Technische Universität Dresden in 2007, where he is now head of the Organic Solar Cell Group. His research concentrates on small-molecule-based organic solar cells, their fundamental working principles, and strategies for device optimization. Karl Leo obtained the Diplomphysiker degree from the University of Freiburg in 1985, working with Adolf Goetzberger at the Fraunhofer-Institut für Solare Energiesysteme. In 1988, he obtained the PhD degree from the University of Stuttgart for a PhD thesis performed at the Max-Planck-Institut für Festkörperforschung in Stuttgart under the supervision of Hans Queisser. From 1989 to 1991, he was a postdoctoral researcher at AT&T Bell Laboratories in Holmdel, NJ, USA. From 1991 to 1993, he was with the Rheinisch-Westfälische Technische Hochschule (RWTH) in Aachen, Germany. Since 1993, he has been full professor of optoelectronics at the Technische Universität Dresden. Since 2002, he is also with the Fraunhofer society, currently as director of Fraunhofer COMEDD. His main current interests are novel semiconductor systems such as semiconducting organic thin films, with special emphasis to understand growth, basic device principles, and the optical response. Recently, he has also worked on device development, such as highly efficient organic LED and solar cells. His work was recognized by several awards, including the Leibniz-Award in 2002. He was involved in the founding of several companies such as Novaled AG and Heliatek GmbH. Figure 1 Operation principles of an OLED (left) and an OSC (right). Two-layer devices are shown. Reprinted with permission from Walzer et al., Chem. Rev. 107, 1233 (2007).

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“…24,25 In fact, an electron-transfer pathway followed by proton transfer has been established for hydride-transfer reactions from 4-(dimethylamino)phenyl meth-ane derivatives, for example, LCV, to 2,3-dichloro-5,6-dicyanop-benzoquinone (DDQ). 26 Thus, the oxidation of LCV by TCNQ is achieved by hydride abstraction. When TCNQ gets hydrogen atoms, TCNQ can be reduced to p-phenylenedimalononitrile (TCNQH 2 ).…”

Section: Resultsmentioning

confidence: 99%

Leuco Crystal Violet as a Dopant for n-Doping of Organic Thin Films of Fullerene C₆₀

et al. 2004

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The triphenylmethane dye crystal violet (CV) and its leuco base, leucocrystal violet (LCV), are investigated as dopants for n-type doping of fullerene C 60 . Conductivities up to 8 × 10 -3 S/cm at 30°C are achieved when C 60 is doped with CV. Mass spectroscopy and optical spectroscopy (UV/VIS/NIR absorption and Fourier transform infrared transmission) confirm that the leuco base LCV is formed during sublimation of the cationic CV dye. When the commercially available LCV was directly used as a dopant in C 60 , a maximum conductivity of 1.3 × 10 -2 S/cm was obtained at 30°C. We found that in both cases, the leuco base became reoxidized to the cationic form by electron transfer to electron-accepting matrixes, leading to the doping effect. The donor properties of LCV in a charge-transfer complex with 7,7,8,8-tetracyanoquinodimethane (TCNQ) were confirmed by UV/VIS/NIR absorption and Fourier transform infrared (FTIR) spectroscopy. C 60 anions were observed in the FTIR or NIR absorption spectra of the mixed films of C 60 and LCV. Photoinduced charge transfer between LCV and C 60 provides free electrons, which increase the n-type conductivity. The electron transfer becomes irreversible by hydride abstraction.

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Mechanism of hydride transfer reaction from 4-(dimethylamino)phenyl methane derivatives to 2,3-dichloro-5,6-dicyano-p-benzoquinone

Cited by 23 publications

References 9 publications

Doping of organic semiconductors

Doping of organic semiconductors

Doping of Organic Semiconductors

Leuco Crystal Violet as a Dopant for n-Doping of Organic Thin Films of Fullerene C₆₀

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Mechanism of hydride transfer reaction from 4-(dimethylamino)phenyl methane derivatives to 2,3-dichloro-5,6-dicyano-p-benzoquinone

Cited by 23 publications

References 9 publications

Doping of organic semiconductors

Doping of organic semiconductors

Doping of Organic Semiconductors

Leuco Crystal Violet as a Dopant for n-Doping of Organic Thin Films of Fullerene C60

Contact Info

Product

Resources

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Leuco Crystal Violet as a Dopant for n-Doping of Organic Thin Films of Fullerene C₆₀