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Bisindeno-annulated pentacenes with exceptionally high photo-stability and ordered molecular packing: simple synthesis by a regio-selective Scholl reaction

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TLDR
This research provides a promising strategy to access stable higher order acenes with controlled molecular order and exhibited exceptionally high photo-stability in the solution, with a half-life time of 11.2 years.
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This article is published in Chemical Communications.The article was published on 2015-02-12. It has received 62 citations till now. The article focuses on the topics: Scholl reaction & Pentacene.

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Citations
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Synthetic Applications of Oxidative Aromatic Coupling – from Biphenols to Nanographenes

TL;DR: Analysis of the progress achieved in this field since 2013 reveals that many groups have contributed by pushing the boundary of structural possibilities, expanding into surface‐assisted (cyclo)dehydrogenation, and developing new reagents.
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Construction of Heptagon-Containing Molecular Nanocarbons

TL;DR: Recent advances in solution-mediated and surface-assisted synthesis of heptagon-containing molecular nanocarbons, as well as the intriguing properties of these frameworks, will be discussed.
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Strategies for the Synthesis of Higher Acenes

TL;DR: The outstanding performance of pentacene‐based molecules in molecular electronics, as well as the predicted enhanced semiconducting properties of extended acenes, have stimulated the development of new synthetic methods and functionalization strategies for the preparation of stable and soluble acenes larger than tetracene with the aim of obtaining improved functional materials.
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Extended Bis(benzothia)quinodimethanes and Their Dications: From Singlet Diradicaloids to Isoelectronic Structures of Long Acenes.

TL;DR: The research gave some insights into the design and synthesis of stable longer acene analogues and their dications can be regarded as genuine isoelectronic structures of pentacenes, hexacene, and heptacene.
References
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Journal ArticleDOI

The larger acenes: versatile organic semiconductors.

TL;DR: New approaches to add functionality were developed to improve the processability of these materials in solution, allowing the synthesis of acenes larger than pentacene, which have hitherto been largely unavailable and poorly studied.
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Comparison of Oxidative Aromatic Coupling and the Scholl Reaction

TL;DR: The authors venture the hypothesis that, depending on the electronic structure of the substrates and the nature of the "catalyst", two different mechanisms can operate, one involves the intermediacy of a radical cation and the other the formation of a sigma complex between the acid and the substrate.
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Functionalized higher acenes: hexacene and heptacene.

TL;DR: Provided a large enough alkyne substituent is used, these large aromatic rods are both stable and soluble and can be characterized spectroscopically as well as by single-crystal X-ray diffraction.
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