Abstract

Rubrene (5,6,11,12-tetraphenyltetracene) is a polyacene material that has been well studied throughout its nearly one-hundred year history. Originally found fascinating for its luminescent properties, it has emerged at the forefront for organic electronics due to its particularly high charge carrier mobility for an organic crystal. Despite great interest and its explosion in the literature over the past two decades, the commercial synthesis of rubrene has remained relatively unchanged since its initial discovery in 1926. Several recent studies have reported alternate routes to the rubrene structure with substitutions on the peripheral­ aromatic rings and tetracene core. Substituting in this manner has the potential to improve upon rubrene’s electronic properties. We review the various routes to rubrene and its derivatives and provide a brief overview of the solid-state library available for study. The information gained by comparing the solid-state properties between derivatives offers insight into unpredictable crystallization and polymorphism – complicated issues – which have hindered research into materials applications­ of rubrene. We hope that these insights inspire work in application­-driven synthetic chemistry for future rubrene derivatives.

1 Introduction

2 Synthesis

2.1 Traditional Rubrene Synthesis

2.1.1 Recent Applications

2.2 Multi-Step Synthesis

2.2.1 Historical Routes

2.2.2 Diels–Alder Approaches

2.2.3 Cross-Coupling Approaches

2.2.4 Comparative Synthesis of Perfluororubrene

3 Crystal Engineering

4 Conclusions and Outlook

Publication History

Received: 03 August 2020

Accepted: 08 September 2020

Publication Date:
28 October 2020 (online)

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

中文翻译：

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钌及其衍生物的合成与晶体工程

摘要

橡胶（5,6,11,12-四苯基并四苯）是一种多并苯材料，在其近一百年的历史中都得到了充分的研究。最初发现其发光特性引人入胜，由于其对有机晶体的特别高的载流子迁移率，它已成为有机电子领域的最前沿。尽管在过去的二十年中人们对它有极大的兴趣并在文学中取得了飞速发展，但自1926年首次发现红荧烯以来，其商业合成一直保持相对不变。最近的一些研究报告了在外围芳香环和环上有取代基的红宝石结构的替代途径。并四苯芯。以这种方式取代具有改善红荧烯的电子性能的潜力。我们回顾了获得红荧烯及其衍生物的各种途径，并简要介绍了可供研究的固态库。通过比较衍生物之间的固态特性而获得的信息提供了对不可预测的结晶和多晶型（复杂的问题）的见解，这些问题阻碍了对红荧烯材料应用的研究。我们希望这些见识能激发人们在应用驱动的合成化学中开发未来的红荧烯衍生物。

1引言

2综合

2.1传统的丁烯合成

2.1.1最近的应用

2.2多步合成

2.2.1历史路线

2.2.2 Diels–Alder方法

2.2.3交叉耦合方法

2.2.4全氟橡胶的比较合成

3水晶工程

4结论与展望

出版历史

收到：2020年

8月3日已接受：2020年9月8日

发布日期：
2020年10月28日（在线）

©2020年。Thieme。版权所有

Georg Thieme Verlag
KGRüdigerstraße14，70469斯图加特，德国