A soluble precursor of hexacene and its application in thin film transistors

Watanabe, Motonori; Su, Wei; Chen, Kew‐Yu; Chien, Ching Ting; Chao, Ting Han; Chang, Yuan Jay; Liu, Shun Wei; Chow, Tahsin J.

doi:10.1039/c3cc00278k

Cited by 20 publications

(21 citation statements)

References 24 publications

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“…The conductivity of crystalline hexacene (2.21 Â 10 À4 S m À1 ) was slightly higher than that of pentacene [32]. The hole mobilities of hexacene thin films have been measured very recently [34].…”

Section: Parent Hexacenementioning

confidence: 99%

Beyond Pentacenes: Synthesis and Properties of Higher Acenes

Tönshoff

Bettinger

2013

Polyarenes I

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Acenes consist of linearly annulated benzene rings. Their reactivity increases quickly with increasing chain length. Therefore acenes longer than pentacene are very sensitive towards oxygen in the presence of light and thus these molecules have not been well studied or have remained elusive in spite of synthetic efforts dating back to the 1930s. This review gives an historical account of the development of the chemistry of acenes larger than pentacene and summarizes the recent progress in the field including strategies for stabilization of higher acenes up to nonacene.

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Section: Parent Hexacenementioning

confidence: 99%

Beyond Pentacenes: Synthesis and Properties of Higher Acenes

Tönshoff

Bettinger

2013

Polyarenes I

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“…subjected 6ac to a Diels–Alder reaction with diethyl malonate under microwave conditions, and from the cycloaddition adduct, 6ac could be generated after annealing in a nitrogen atmosphere at 240 °C (Scheme 1 b). [63] In this way, it was possible to obtain films of 6ac by means of spin coating and to fabricate OFET devices that showed low hole mobility, which was suggested to result from the low quality of the films [63] . The best results obtained after optimization were 3.5×10 −2 cm 2 V −1 s −1 [63] .…”

Section: Hexacene and Heptacene In Bulk Phasesmentioning

confidence: 99%

“… [63] In this way, it was possible to obtain films of 6ac by means of spin coating and to fabricate OFET devices that showed low hole mobility, which was suggested to result from the low quality of the films [63] . The best results obtained after optimization were 3.5×10 −2 cm 2 V −1 s −1 [63] . The same group also used 6ac obtained by the decarbonylation route for the fabrication of OFETs by means of vacuum deposition and obtained a hole mobility of 7.6×10 −2 cm 2 V −1 s −1 [64] .…”

Section: Hexacene and Heptacene In Bulk Phasesmentioning

confidence: 99%

Pushing the Limits of Acene Chemistry: The Recent Surge of Large Acenes

Tönshoff

Bettinger

2020

Chemistry A European J

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Acenes, consisting of linearly fused benzene rings, are an important fundamental class of organic compounds with various applications. Hexacene is the largest acene that was synthesized and isolated in the 20th century. The next largest member of the acene family, heptacene, was observed in 2007 and since then significant progress in preparing acenes has been reported. Significantly larger acenes, up to undecacene, could be studied by means of low‐temperature matrix isolation spectroscopy with in situ photolytic generation, and up to dodecacene by means of on‐surface synthesis employing innovative precursors and highly defined crystalline metal surfaces under ultrahigh vacuum conditions. The review summarizes recent experimental and theoretical advances in the area of acenes that give a significantly deeper insight into the fundamental properties and nature of the electronic structure of this fascinating class of organic compounds.

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“…By this strategy, pentacene‐based films have been accessed by means of thermally induced retro‐Diels–Alder reactions from spin‐coated solutions of the corresponding cycloadducts with different dienophiles including N ‐sulfinylbutylcarbamates, dialkyl azodicarboxylates, or diethyl ketomalonate, which was also used to prepare a soluble precursor of hexacene . The thermal elimination of lactam bridges has also been applied to the synthesis of other related PAHs such as twistacenes, which are benzo‐fused acene derivatives bearing rigid terminal pyrene units …”

Section: Acenes Through Retrocycloadditionmentioning

confidence: 99%