Synthesis of pentacene-, tetracene- and anthracene bisimides using double-cyclization reaction mediated by bismuth(iii) triflate

Katsuta, Shuhei; Tanaka, Kazuki; Maruya, Yukihiro; Mori, Shigeki; Masuo, Sadahiro; Okujima, Tetsuo; Uno, Hidemitsu; Nakayama, Keiichi I.; Yamada, Hiroko

doi:10.1039/c1cc13980k

Cited by 95 publications

(56 citation statements)

References 25 publications

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“…The analogous reaction sequence with anthracene-9,10-dicarboxylic acid or pentacene-6,13-dicarboxylic acid affords the inversion-symmetric acene diimides 77 [93] and 78. [92] Moderate electron mobilities of 10 À3 cm 2 V À1 s À1 were reported for a derivative of 76 (R 1 = C 6 H 13 ). The condensation of NDI and PDI derivatives across their core positions was developed by Marder, Wang, and coworkers.…”

Section: Lateral Ring Expansionmentioning

confidence: 96%

“…An approach to unsubstituted tetracene diimides, which is, however, not based on naphthalene diimide but the imide groups are instead introduced to the tetracene scaffold by this approach, was presented by Yamada and co-workers. [92] The synthesis starts with tetracene-5,12-dicarboxylic acid, which is accessible by oxidation of the respective dialdehyde. After activation of the acid groups to acid chlorides, the resulting intermediate could be cyclized with an alkylisocyanate in the presence of a Lewis acid to give the tetracene diimide 76.…”

Section: Lateral Ring Expansionmentioning

confidence: 99%

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Strategies for the Synthesis of Functional Naphthalene Diimides

2014

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Naphthalene diimides, which have for a long time been in the shadow of their higher homologues the perylene diimides, currently belong to the most investigated classes of organic compounds. This is primarily due to the initial synthetic studies on core functionalization that were carried out at the beginning of the last decade, which facilitated diverse structural modifications of the naphthalene scaffold. Compounds with greatly modified optical and electronic properties that can be easily and effectively modulated by appropriate functionalization were made accessible through relatively little synthetic effort. This resulted in diverse interesting applications. The electron-deficient character of these compounds makes them highly valuable, particularly in the field of organic electronics as air-stable n-type semiconductors, while absorption bands over the whole visible spectral range through the introduction of core substituents enabled interesting photosystems and photovoltaic applications. This Review provides an overview on different approaches towards core functionalization as well as on synthetic strategies for the core expansion of naphthalene diimides that have been developed mainly in the last five years.

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Section: Lateral Ring Expansionmentioning

confidence: 96%

Section: Lateral Ring Expansionmentioning

confidence: 99%

Strategies for the Synthesis of Functional Naphthalene Diimides

2014

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“…28, 29 The lateral extension of the π-conjugation system based on NDI, on the other hand, has been examined with the inclusion of fused aromatic rings, such as benzene, 30,31 thiophene, 32 thiazole, 33 benzo[b]thiophene, 34 benzo[b]pyrrole, 35,36 quinoxaline, 37,38 and so on ( Figure 1). This approach, in contrast to the former vertical extension, is an interesting way to control the electronic structure of the resulting core-extended NDI (cNDI) derivatives; the LUMO of the system tends to localize on the NDI skeleton, whereas the highest molecular orbital (HOMO) tends to delocalize in the lateral direction through the naphthalene 2-, 3-, 6-, and 7-carbon atoms.…”

mentioning

confidence: 99%

Thiophene-Fused Naphthalene Diimides: New Building Blocks for Electron Deficient π-Functional Materials

Takimiya

Nakano

2017

Bulletin of the Chemical Society of Japan

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Development of novel π-conjugated building blocks that can be integrated into molecular or macromolecular systems is key to the evolution of new superior organic semiconductors utilized as the active materials in organic electronics devices such as organic field-effect transistors (OFETs), organic photovoltaics (OPVs), and organic thermoelectric (TE) devices. This review affords a brief overview of thiophene-fused naphthalene diimide (NDI), namely naphtho[2,3-b:6,7-b¤]dithiophene diimide (NDTI) and naphtho [2,3-b]thiophene diimide (NTI), recently developed as novel electron deficient building blocks for n-type and ambipolar organic semiconductors. These thiophene-fused NDI building blocks had not been known until 2013 owing to their synthetic difficulty; more precisely, the difficulty in attaching fused-thiophene ring(s) on the NDI core. We have successfully established a thiophene-annulation reaction on ethyne-substituted NDI derivatives, which allows us to elaborate various NDTI and NTI derivatives. The key features of these building blocks are low-lying energy levels of lowest unoccupied molecular orbitals (LUMO, 3.84.1 eV below the vacuum level) and easy functionalizability of the thiophene ¡-positions, which allows their derivatives and polymers to conjugate efficiently with additional π-and comonomer units. These features make the NDTI-and NTIderivatives and polymers promising n-type and ambipolar materials for OFETs and acceptors for OPVs. In fact, various useful materials have already been derived from the NDTI and NTI building blocks: air-stable n-type small molecules and polymers with high electron mobility (³0.8 cm 2 V ¹1 s ¹1), ambipolar oligomers and polymers with well-balanced hole and electron mobilities, doped n-type semiconductors affording bulk conductors applicable to n-type TE materials, and electron acceptor molecules and polymers for OPVs showing promising power conversion efficiencies of up to 9%. These impressive and diversified device performances testify the usefulness of thiophene-fused NDI building blocks in the development of new electron deficient π-functional materials.

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“…The improved performance of 265d was attributed to the low-lying LUMO energy level induced by the nitrile groups. Angular-shaped tetracene-and pentacene-bisimides, 266 and 267 were synthesized via a similar double-cyclization reaction [346]. Vapor deposited films of 266b showed low electron mobility of 3.3 × 10 −3 cm 2 V −1 s −1 .…”

Section: Perylene Diimide and Derivativesmentioning

confidence: 99%

Organic Semiconductors for Field-Effect Transistors

Zhang

2015

Lecture Notes in Chemistry

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An important application of organic semiconductors is to fabricate organic field-effect transistors (OFETs) which are essential building blocks for the next generation of organic circuits. In terms of molecular size or molecular weight, organic semiconductors can be divided into small-molecule and polymer semiconductors, and thus their corresponding OFETs can also be categorized into organic small molecule OFETs and polymer field-effect transistors (PFETs). On the basis of the main charge carriers transporting in OFET channels, organic semiconductors can be further divided into p-type, n-type, and ambipolar semiconducting materials. According to the characteristic of the organic semiconductors, the OFETs can be classified into two types: organic thin film transistors (OTFTs) and organic single crystal transistors. In any kind of OFET devices, organic semiconductor materials are the core; their properties determine the performance of the electronic devices. Therefore, the design and synthesis of high performance organic semiconductor materials are the basis and premise of the wide application of OFET devices. In the past few decades, great progress has been made in developing organic semiconductors. Besides organic semiconducting materials, there are many other factors influencing the performance of OFETs including device configuration, processing technique, and other devices physical factors, etc. In the following, a brief review of the development of p-type, n-type, ambipolar organic semiconductors and their field-effect properties is given. The history, mechanism, configuration, and fabrication methods of OFET devices and main performance influencing factors of OFETs are also introduced.

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Synthesis of pentacene-, tetracene- and anthracene bisimides using double-cyclization reaction mediated by bismuth(iii) triflate

Cited by 95 publications

References 25 publications

Strategies for the Synthesis of Functional Naphthalene Diimides

Strategies for the Synthesis of Functional Naphthalene Diimides

Thiophene-Fused Naphthalene Diimides: New Building Blocks for Electron Deficient π-Functional Materials

Organic Semiconductors for Field-Effect Transistors

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