One-Pot Synthesis of Stable NIR Tetracene Diimides via Double Cross-Coupling

Yue, Wan; Gao, Jing; Li, Yan; Ji, Wei; Motta, Simone Di; Negri, Fabrizia; Wang, Zhaohui

doi:10.1021/ja207630a

Cited by 98 publications

(65 citation statements)

References 35 publications

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“…The analogous tetrabenzotetracene derivative 74 a was prepared by Wang and co-workers through a double Stille cross-coupling reaction. [91] The synScheme 13. Expansion of the NDI core to derivatives with an azaacene core.…”

Section: Lateral Ring Expansionmentioning

confidence: 99%

“…[91] Thus, the core-expanded NDIs with structure 75 obtained in this way bear substituents at the tetracene core that are predefined by the substituent pattern of the employed metallacycles. The spatial proximity of these substituents to the imide oxygen atoms evokes a twisting of the tetracyclic scaffold, as evident from a single-crystal structure.…”

Section: Lateral Ring Expansionmentioning

confidence: 99%

“…[91,96] The exchange of angularly condensed benzene rings by thiophene rings in derivative 73 a again evokes a bathochromic shift of the absorption maximum (l = 655 nm in chloroform). [90] The oxidized heteroacene diimides 69 a and 70 a display absorptions with band edges at about 600 nm.…”

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confidence: 98%

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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: 99%

Section: Lateral Ring Expansionmentioning

confidence: 99%

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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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“…On the one hand, the optical properties of the rylene diimide-based system can be tuned by the central rylene moiety [5,6], i.e., increasing the number of naphthalene moieties (Figure 1b) can drastically alter the absorption range from ultraviolet to visible and to the infrared region. On the other hand, the lateral extension of the π-conjugation system based on NDI, the smallest rylene diimide molecule, has also been examined by fusing different aromatic rings, such as benzene [7][8][9], thiophene [10], thiazole [11], benzo [b]thiophene [12], quinoxaline [13,14], benzo [b]pyrrole [15], and so on ( Figure 1c). In contrast to the former vertical π-extension, the latter approach is a promising way of controlling the electronic structure of the resulting core-extended NDI derivatives because the lowest unoccupied molecular orbital (LUMO) of the system tends to localize on the NDI skeleton, i.e., the vertical molecular axis, whereas the highest occupied molecular orbital (HOMO) tends to delocalize in the lateral direction through the naphthalene 2-, 3-, 6-, and 7-carbon atoms.…”

Section: Introductionmentioning

confidence: 99%

N,N′-Bis(2-cyclohexylethyl)naphtho[2,3-b:6,7-b′]dithiophene Diimides: Effects of Substituents

2016

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Naphtho[2,3-b:6,7-b 1 ]dithiophene-4,5,9,10-tetracarboxylic diimide (NDTI) is a promising electron-deficient building block for n-type organic conductors, and the performance of NDTI-based field-effect transistors (FETs) is largely dependent on the substituents that alter the supramolecular organization in the solid state and, in turn, the intermolecular orbital overlap. For this reason, the rational selection of substituent on imide nitrogen atoms and/or thiophene α-positions is the key to developing superior n-type organic semiconductors. We here report new NDTI derivatives having N-(2-cyclohexylethyl) groups. Despite their one-dimensional packing structures in the solid state regardless of the presence or absence of chlorine groups at the thiophene α-positions, their FETs show promising performance with electron mobilities higher than 0.1 cm 2¨V´1¨s´1 under ambient conditions. We also discuss how the cyclohexylethyl groups affect the packing structure in comparison with analogous n-octyl derivatives having the same number of carbon atoms.

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One-Pot Synthesis of Stable NIR Tetracene Diimides via Double Cross-Coupling

Cited by 98 publications

References 35 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

N,N′-Bis(2-cyclohexylethyl)naphtho[2,3-b:6,7-b′]dithiophene Diimides: Effects of Substituents

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