Sexterrylenetetracarboxylic Bisimides: NIR Dyes

Langhals, Heinz; Zgela, Dominik; Lüling, Robin

doi:10.1021/acs.joc.5b02092

Cited by 21 publications

(15 citation statements)

References 24 publications

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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.…”

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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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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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“…Both effects have already been reported as origin of bathochromic shifts. [15,46,47] Expanding the macrocycle with a triazole subunit in 2 however reduces the intensity of the signals above 320 nm considerably and the UV spectrum of 2 (maximum at 289 nm with a shoulder at about 316 nm) almost resembles the one of the open precursor 24. The fact that macrocycle 2, comprising a triazole in its periphery, is at least as rigid as the macrocycle 1 challenges the fixation of the system as major contribution to the bathochromic shift.…”

Section: Uv/vis Spectroscopymentioning

confidence: 99%

A Phenyl‐Ethynyl‐Macrocycle: A Model Compound for “Geländer” Oligomers Comprising Reactive Conjugated Banisters

et al. 2018

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Macrocycle 1 is assembled as smallest member of a series of “Geländer” oligomers with a conjugated banister comprising exclusively sp2‐ and sp‐hybridized carbon atoms. The synthesis of 1 is based on an acetylene scaffolding approach, comprising Sonogashira cross‐coupling reactions in combination with protection group strategies and a final cyclization based on an oxidative acetylene coupling using Eglinton‐Breslow reaction conditions. Macrocycle 1 serves as model compound for the investigation of the structural integrity of the strained 1,3‐diyne subunit. An enhanced reactivity of the strained 1,3‐diyne subunit is documented by its engagement in Huisgen's (2+3) cycloaddition when exposed to an azide at elevated temperature. Both structures, macrocycle 1 and cycloaddition‐product 2, are fully characterized including their solid‐state structure obtained by X‐ray diffraction analysis.

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“…Compared with fruitful researches of oligorylene-bisimides for organic devices and single molecular spectroscopy [1][2][3][4][5][6], genuine oligorylenes have been sporadically investigated mainly because of their synthetic difficulty and low solubility ( Figure 1) [7]. To be applied to electronic or photovoltaic components, the scalable synthesis of pure soluble compounds is essential.…”

Section: Introductionmentioning

confidence: 99%

Direct borylation of terrylene and quaterrylene

Kano

Uehara

Matsuo

et al. 2020

Beilstein J. Org. Chem.

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The preparation of large rylenes often needs the use of solubilizing groups along the rylene backbone, and all the substituents of the terrylenes and quaterrylenes were introduced before creating the rylene skeleton. In this work, we successfully synthesized 2,5,10,13-tetrakis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)terrylene (TB4) by using an iridium-catalyzed direct borylation of C–H bonds in terrylene in 56% yield. The product is soluble in common organic solvents and could be purified without column chromatography. Single crystal X-ray diffraction analysis revealed that the terrylene core is not disturbed by the substituents and is perfectly flat. The photophysical properties of TB4 are also unchanged by the substituents because the carbon atoms at 2,5,10,13-positions have less coefficients on its HOMO and LUMO, estimated by theoretical calculations. Finally, the same borylation reaction was applied for quaterrylene, resulting in the formation of soluble tetra-borylated quaterrylene despite a low yield. The post modification of rylenes enables us to prepare their borylated products as versatile units after creating the rylene skeletons.

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Sexterrylenetetracarboxylic Bisimides: NIR Dyes

Cited by 21 publications

References 24 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

A Phenyl‐Ethynyl‐Macrocycle: A Model Compound for “Geländer” Oligomers Comprising Reactive Conjugated Banisters

Direct borylation of terrylene and quaterrylene

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