Improved stability in N-alkylated organic semiconductors for thin film transistors: Synthesis and characterization of N,N′-dialkylated dihydrodiazapentacene derivatives

Itoh, Tetsuji; Aomori, Shigeru; Oh‐e, Masahito; Koden, Mitsuhiro; Arakawa, Yasuhiko

doi:10.1016/j.synthmet.2012.05.014

Cited by 10 publications

(13 citation statements)

References 37 publications

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“…Azaacenes, the nitrogen‐substituted analogues of acenes, have attracted much attention in the field of organic electronics as promising candidates for charge‐transport materials because of their facile syntheses and higher chemical stability compared with larger acenes, such as pentacene 1. Over the past decade, several research groups have reported the synthesis of novel azaacene derivatives by means of chemical modification of azaacene skeletons, for example, by introducing functional groups2, 3 and/or extending the π‐plane 4. However, there have been few attempts to construct complicated structures by combining azaacene molecules, in spite of their potential for three‐dimensional π‐conjugated molecular bricolages.…”

Section: Methodsmentioning

confidence: 99%

A Facile and Versatile Approach to Double N‐Heterohelicenes: Tandem Oxidative CN Couplings of N‐Heteroacenes via Cruciform Dimers

et al. 2015

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Novel double N-hetero[5]helicenes that are composed of two nitrogen-substituted heteropentacenes are synthesized by tandem oxidative CN couplings via the cruciform heteropentacene dimers. The developed method is very facile and enables the synthesis of a double helicene in only two steps from commercially available naphthalene derivatives. These double N-hetero[5]helicenes have larger torsion angles in the fjord regions than typical [5]helicenes, and optical/electrochemical measurements revealed a significant increase in the electronic communication between the two heteropentacene moieties of the double helicenes compared with their cruciform dimers. The optical resolution of one of the double helicenes was successfully carried out, and their stability towards racemization was remarkably higher than those of typical [5]helicenes. The synthetic strategy proposed in this paper should be versatile and widely applicable to the preparation of double helicenes from other N-containing π-conjugated planar molecules.

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Section: Methodsmentioning

confidence: 99%

A Facile and Versatile Approach to Double N‐Heterohelicenes: Tandem Oxidative CN Couplings of N‐Heteroacenes via Cruciform Dimers

et al. 2015

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“…With a HOMO energy level of −5.01 eV for 22a and −4.79 eV for 22b , they both functioned as p‐type semiconductors in OFETs fabricated on thin crystals showing low field‐effect mobilities in the range of 10 −4 cm 2 V −1 s −1 . A similar alkylation reaction of 2 yielded 23 , which has a HOMO energy level of −4.76 eV . As found from the single crystal structure, 23 has a planar π‐backbone and exhibits offset π‐stacking with a π‐to‐π distance of about 3.5 Å.…”

Section: Other N‐heteropentacene Derivativesmentioning

confidence: 99%

Ten Years of N‐Heteropentacenes as Semiconductors for Organic Thin‐Film Transistors

2014

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Introducing N atoms to the pentacene backbone leads to N-heteropentacenes, whose properties can be tuned by changing the number, position and valence state of N atoms in the pentacene backbone. With a rapid development in recent years, N-heteropentacenes and their derivatives have arisen as a new family of organic semiconductors with high performance in organic thin-film transistors (OTFTs). This article reviews the research efforts of developing N-heteropentacenes into organic semiconductors starting from 2003 with emphasis on the work of the author's group since 2009. The structure-property relationship and design rationale are highlighted based on an overview of reported organic semiconductors of N-heteropentacenes.

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“…Thea bsorption spectra of 1a, 3a,a nd 6,13-dihexyl-6,13dihydro-6,13-diazapentacene [3] (7)a re shown in Figure 2a. Thespectral shape for cruciform dimer 3a was very similar to that of 7,a nd therefore,t he two DP units in 3a basically maintain their monomeric electronic properties because of their perpendicular arrangement.…”

Section: Methodsmentioning

confidence: 99%

“…[1] Over the past decade,s everal research groups have reported the synthesis of novel azaacene derivatives by means of chemical modification of azaacene skeletons,f or example,b yi ntroducing functional groups [2,3] and/or extending the p-plane. [1] Over the past decade,s everal research groups have reported the synthesis of novel azaacene derivatives by means of chemical modification of azaacene skeletons,f or example,b yi ntroducing functional groups [2,3] and/or extending the p-plane.…”

mentioning

confidence: 99%

“…Azaacenes,the nitrogen-substituted analogues of acenes, have attracted much attention in the field of organic electronics as promising candidates for charge-transport materials because of their facile syntheses and higher chemical stability compared with larger acenes,s uch as pentacene. [1] Over the past decade,s everal research groups have reported the synthesis of novel azaacene derivatives by means of chemical modification of azaacene skeletons,f or example,b yi ntroducing functional groups [2,3] and/or extending the p-plane. [4] However,there have been few attempts to construct complicated structures by combining azaacene molecules,i ns pite of their potential for three-dimensional p-conjugated molecular bricolages.H erein, we report the shortest synthesis of double N-hetero [5]helicenes by adirect oxidative coupling of N-substituted pentacenes via their cruciform dimers to demonstrate the usefulness of these compounds as building blocks for novel three-dimensional (3D) p-systems (Scheme 1).…”

mentioning

confidence: 99%

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A Facile and Versatile Approach to Double N‐Heterohelicenes: Tandem Oxidative CN Couplings of N‐Heteroacenes via Cruciform Dimers

et al. 2015

View full text Add to dashboard Cite

Novel double N-hetero [5]helicenes that are composed of two nitrogen-substituted heteropentacenes are synthesized by tandem oxidative CÀNc ouplings via the cruciform heteropentacene dimers.T he developed method is very facile and enables the synthesis of adouble helicene in only two steps from commercially available naphthalene derivatives.T hese double N-hetero[5]helicenes have larger torsion angles in the fjord regions than typical [5]helicenes,a nd optical/electrochemical measurements revealed as ignificant increase in the electronic communication between the two heteropentacene moieties of the double helicenes compared with their cruciform dimers.T he optical resolution of one of the double helicenes was successfully carried out, and their stability towards racemization was remarkably higher than those of typical [5]helicenes.T he synthetic strategy proposed in this paper should be versatile and widely applicable to the preparation of double helicenes from other N-containing p-conjugated planar molecules.

show abstract

Improved stability in N-alkylated organic semiconductors for thin film transistors: Synthesis and characterization of N,N′-dialkylated dihydrodiazapentacene derivatives

Cited by 10 publications

References 37 publications

A Facile and Versatile Approach to Double N‐Heterohelicenes: Tandem Oxidative CN Couplings of N‐Heteroacenes via Cruciform Dimers

A Facile and Versatile Approach to Double N‐Heterohelicenes: Tandem Oxidative CN Couplings of N‐Heteroacenes via Cruciform Dimers

Ten Years of N‐Heteropentacenes as Semiconductors for Organic Thin‐Film Transistors

A Facile and Versatile Approach to Double N‐Heterohelicenes: Tandem Oxidative CN Couplings of N‐Heteroacenes via Cruciform Dimers

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