Facile Synthesis, Structure, and Properties of Benzo[1,2-<i>b</i>:4,5-<i>b</i>‘]dichalcogenophenes

Takimiya, Kazuo; Konda, Yasushi; Ebata, Hideaki; Niihara, Naoto; Otsubo, Tetsuo

doi:10.1021/jo051812m

Cited by 153 publications

(105 citation statements)

References 23 publications

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“…Prior to studies of the NDTI-and NTI-building blocks, our research group engaged in the development of p-type molecular and polymer semiconductors based on acenedithiophenes, such as benzo-[1,2-b:4,5-b¤]dithiophene (BDT), 41,42 naphtho[2,3-b:6,7-b¤]-dithiophene (NDT), 4346 and anthra[2,3-b:6,7-b¤]dithiophene (ADT) 47 building blocks ( Figure 2) taking advantage of their high-lying HOMO energy levels (E HOMO ). On the other hand, their application to the development of n-type organic semiconductors has also been examined with the introduction of strong electron withdrawing substituents 48 or quinoidalization terminated with electron deficient groups.…”

Section: Synthesis Of Ndti and Nti Derivativesmentioning

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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Section: Synthesis Of Ndti and Nti Derivativesmentioning

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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“…14 This material is formally isoelectronic with pyrene (20), but replacement of the two benzene rings of pyrene with thiophenes greatly perturbs the Kekulé resonance structure (Chart 5). In fact, the Frontier MO energies of the naphthodithiophene 14 (HOMO À4:98 eV and LUMO À1:87 eV) on DFT calculation at the B3LYP-6-31G ( it has a greater electron-donating ability than pyrene and forms highly conductive molecular complexes with iodine or DDQ.…”

Section: ç Diarylnaphthodithiophenes As Highperformance P-channel Semmentioning

confidence: 99%

“…Scheme 1 shows a ready synthetic method of 21 and 22 that was successfully developed by our group. 17,20 This three-step synthetic method is quite straightforward and has a high overall yield; therefore, it is attractive for materials synthesis. The last step involves a unique heterocyclization reaction to give either 21 or 22 depending on the sulfur and selenium reagents employed in the process.…”

Section: ç Diarylbenzodichalcogenophenes Asmentioning

confidence: 99%

Development of New Semiconducting Materials for Durable High-performance Air-stable Organic Field-effect Transistors

Takimiya¹,

Kunugi

Otsubo³

2007

Chemistry Letters

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133

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New thiophene-and selenophene-fused aromatic compounds were successfully developed as high-performance semiconducting materials for organic field-effect transistors (OFETs). Among them, the most advanced compounds designed on consideration of structure-function relationship showed durable air-stable FET performance. This article highlights the research strategy and development of these superior compounds as well as the molecular factors for the improvement of mobility, sensitivity, and stability, which are very informative for the design of practical semiconductors. Ç IntroductionOrganic field-effect transistors (OFETs) have attracted much attention in the context of inexpensive, flexible, large-area electronics devices such as bendable displays, electronic paper, smart cards, ID tags, and sensors.1 To realize their commercial application, however, OFETs require further improvements in device performance to ensure that they at least match the performance of conventional amorphous silicon-based transistors. Improvements in OFET performance are currently being driven by two different approaches: the optimization of device structures and the development of new organic semiconductors. In terms of device structure, it is noteworthy that device optimization for pentacene (1) (Chart 1) markedly enhanced the initially reported hole mobility 2 of 0.002 cm 2 V À1 s À1 to the most recently obtained value 3 of 3.0 cm 2 V À1 s À1 , the highest among thin film organic semiconducting materials. Furthermore, a stateof-the-art single crystal device using rubrene (2) set the mobility record for OFETs (15-20 cm 2 V À1 s À1 ); 4 however, such device optimization on the basis of known semiconducting materials appears to be limited as far as improvements to mobility are concerned. In contrast, the development of new organic semiconductors has the potential to lead to a breakthrough in OFET development in all respects of carrier mobility, sensitivity, and stability. For this reason, new organic semiconductors are currently being intensively studied, resulting in the development of a growing number of high-performance semiconducting materials with higher mobilities than that of amorphous silicon (0.1 cm 2 V À1 s À1 ); however, almost all organic semiconductors share the severe drawback of being unstable in device operation, resulting in poor reliability and durability. A major challenge in OFET research is therefore the development of practical OFET materials that ensure not only high performance but also high stability in the operational environment. This is a formidable task as the development of such OFET materials requires not only the design of air-, photo-, and thermostable semiconducting molecules but also the precise control of molecular ordering in the thin film phase. For the time being, however, there are no definite guidelines for ''molecular engineering designs'' that are capable of forming interactive networks advantageous for charge migration. As part of our strong interest in modern molecular electronics materia...

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“…[2][3][4] Heteroatoms like sulfur, oxygen, nitrogen etc. change electronic properties of the conductive polymer when their lone electron pair is conjugated with the rest of the molecule in particular with the molecular backbone.…”

Section: Introductionmentioning

confidence: 99%

Electrochromic Properties of Novel Selenophene and Tellurophene Derivatives Based on Carbazole and Triphenylamine Core

et al. 2017

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and Data, Przemyslaw (2017) 'Electrochromic properties of novel selenophene and tellurophene derivatives based on carbazole and triphenylamine core.', The journal of physical chemistry C., 121 (21). pp. 11027-11036. Further information on publisher's website:https://doi.org/10.1021/acs.jpcc.7b00216Publisher's copyright statement:This document is the Accepted Manuscript version of a Published Work that appeared in nal form in The journal of physical chemistry C, copyright c American Chemical Society after peer review and technical editing by the publisher. To access the nal edited and published work see https://doi.org/10.1021/acs.jpcc.7b00216Additional information: Use policyThe full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.Please consult the full DRO policy for further details. Se and Te atoms do not conjugate their lone electron pairs with the -conjugated system and therefore only increase the contribution of the quinoid form of chalcogenophene unit. 2,7-substituted carbazole derivatives present stronger carbazole-chalcogenophene conjugation than 3,6-substituted derivatives. One 3,6-substituted carbazole derivative and triphenylamine derived polymers were found to have promising electrochromic properties with black electrochromism.

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Facile Synthesis, Structure, and Properties of Benzo[1,2-b:4,5-b‘]dichalcogenophenes

Cited by 153 publications

References 23 publications

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

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

Development of New Semiconducting Materials for Durable High-performance Air-stable Organic Field-effect Transistors

Electrochromic Properties of Novel Selenophene and Tellurophene Derivatives Based on Carbazole and Triphenylamine Core

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