Synthesis and Molecular Properties of Four Isomeric Dialkylated Angular-Shaped Naphthodithiophenes

Cheng, Sheng Wen; Chiou, De Yang; Lai, Yinchieh; Yu, Ruo Han; Lee, Chia-Hao; Cheng, Yen‐Ju

doi:10.1021/ol4025953

Cited by 49 publications

(34 citation statements)

References 37 publications

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“…61,62 In the realm of organic electronics, base catalysed isomerisation of alkynylated oligomers to polyaromatic semiconductors has been used for the synthesis of coronenes 63,64,65,66 and thienoacenes of various number of rings and sulfur atoms. 67,68,69,70 Here, we demonstrate that this strategy is also suitable for the synthesis of bis-[(1,2)(5,6)]indoloanthracene (4) a new π-extended nitrogen based heterocycle.…”

Section: Computational Detailsmentioning

confidence: 83%

Highly Luminous Sky-Blue Organic Light-Emitting Diodes Based on the Bis[(1,2)(5,6)]indoloanthracene Emissive Layer

et al. 2016

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An in-depth analysis of the electro-optical and light emissive properties was carried out with a new fused heteroacene, the bis [(1,2)(5,6)] indoloanthracene. The compound was synthesized in a straightforward bidirectional manner from 1,4-dibromo-2,5-diodobenzene utilizing a reaction cascade of isomerisation and cyclisation sequences. Bis-[(1,2)(5,6)] indoloanthracene exhibits bright luminescence with high quantum yield in solution as well as in the solid state. By using this novel semiconductor as active layer, an efficient OLED has been fabricated for which its emission pattern resembles at least two emitters in a single emissive region originated from the same molecule. One has its origin from the single molecule and is similar to the luminescence spectra in solution, whereas the other functions through the formation of aggregates being similar with the emission pattern found with crystals of bis-[(1,2)(5,6)]indoloanthracene. As a result bright sky-blue OLEDs with very high luminance exceeding 10000 cd/m 2 were obtained. Such color pattern and performance has not previously been observed with low molecular weight, electron-rich fused polycyclic aromatic compounds and indicate a promising new class of materials for development.

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Section: Computational Detailsmentioning

confidence: 83%

Highly Luminous Sky-Blue Organic Light-Emitting Diodes Based on the Bis[(1,2)(5,6)]indoloanthracene Emissive Layer

et al. 2016

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“…It should also be noted that the position of the substituents also affects the extent of the E HOMO shift. When comparing the 4,9‐ and 5,10‐dialkyl derivatives, a smaller shift of E HOMO was observed for the 5,10‐derivative . This can be qualitatively explained by the fact that the electron density of the HOMO of NDT3 is smaller at the 5‐ and 10‐positions than at the 4‐ and 9‐positions.…”

Section: Key Synthetic Achievements For the Development Of Ndt‐based mentioning

confidence: 84%

“…Since 2010, different approaches to the synthesis of linear‐fused NDT derivatives have been independently developed by several groups, each of which includes a distinct key reaction such as: (1) sodium sulfide (Na 2 S)‐promoted thienannulation reaction of an o ‐ethynyl‐halobenzene substructure (Scheme ), [15a,16a,20] (2) acid‐induced cyclodehydration of alkyloxy‐substituted naphthalenes to form fused thiophene rings (Scheme ), (3) intramolecular Knoevenagel condensation and dehydration to form fused thiophene rings on a naphthalene core followed by a decarboxylation reaction (Scheme ), and (4) base‐induced tandem 6π cyclization to form the central naphthalene ring from enediyne moieties (Scheme ) …”

Section: Key Synthetic Achievements For the Development Of Ndt‐based mentioning

confidence: 99%

Naphthodithiophenes: Emerging Building Blocks for Organic Electronics

Takimiya

Osaka

2014

The Chemical Record

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Linear-fused naphthodithiophenes (NDTs) are emerging building blocks in the development of new semiconducting small molecules, oligomers, and polymers. The promising nature of NDT-based materials as organic semiconductors has been demonstrated by superior device characteristics in organic field-effect transistors (OFETs) and organic photovoltaics (OPVs) in the last few years. In particular, it is quite impressive that a power conversion efficiency as high as 8.2% has been achieved for a single-junction OPV cell consisting of NDT-based semiconducting polymers and a fullerene derivative in such a short period of time. Here, we provide an overview of recent synthetic evolutions in NDT chemistry and progress in NDT-based materials, especially conjugated oligomers and polymers and their applications to OFETs and OPVs.

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“…78 Although high yields are usually obtained in these reactions, quite harsh conditions are required. The base-mediated cycloaromatization has been applied to the synthesis of the alkaloid tylophorine, 79 coronene derivatives acting as telomerase inhibitors, 80 angular-shaped anthradiselenophenes 81 and naphthodithiophenes 82 with promising optoelectronic applications, thienoacenes 53 and ethene-bridged terthiophenes. 83 …”

Section: Scheme 12 Acid-promoted Cycloaromatization Of O-(alkynyl)bimentioning

confidence: 99%

1,3-Dien-5-ynes: Versatile Building Blocks for the Synthesis of Carbo- and Heterocycles

et al. 2016

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ABSTRACT:1,3-Dien-5-ynes have been extensively used as starting materials for the synthesis of a wide number of different carbo-and heterocycles. The aim of this review is to give an overview of their utility in organic synthesis, highlighting the variety of compounds that can be directly accessed from single reactions over these systems. Thus, cycloaromatization processes are initially commented, followed by reactions directed towards the syntheses of five-membered rings, other carbocycles and, finally, heterocycles. The diverse methodologies that have been developed for the synthesis of each of these types of compounds from 1,3-dien-5-ynes are presented, emphasizing the influence of the reaction conditions and the use of additional reagents in the outcome of the transformations.2

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Synthesis and Molecular Properties of Four Isomeric Dialkylated Angular-Shaped Naphthodithiophenes

Cited by 49 publications

References 37 publications

Highly Luminous Sky-Blue Organic Light-Emitting Diodes Based on the Bis[(1,2)(5,6)]indoloanthracene Emissive Layer

Highly Luminous Sky-Blue Organic Light-Emitting Diodes Based on the Bis[(1,2)(5,6)]indoloanthracene Emissive Layer

Naphthodithiophenes: Emerging Building Blocks for Organic Electronics

1,3-Dien-5-ynes: Versatile Building Blocks for the Synthesis of Carbo- and Heterocycles

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