Acenes beyond organic electronics: sensing of singlet oxygen and stimuli-responsive materials

• Published in: Organic & biomolecular chemistry 2020-11, Vol.18 (45), p.9191-929
• Main Authors: Brega, Valentina, Yan, Yu, Thomas, Samuel W
• Format: Article
• Language: English
• Subjects: Cycloaddition; Cytotoxicity; Dienes; Drug delivery; Drug delivery systems; Drug development; Electronics; Optoelectronics; Oxygen; Physical characteristics; Physical properties; Reactive oxygen species; Singlet oxygen; Stimuli
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/d0ob01744b

The spectroscopic, electronic, and geometrical properties of acenes have enabled their broad applicability in organic optoelectronics. Beyond these physical characteristics of acenes, acenes also offer characteristic and predictable reaction chemistry, especially their behavior as dienes in cycloaddition reactions. Although these cycloaddition reactions, especially those with singlet oxygen ( 1 O 2 ) as the dienophile, are detrimental for organic electronics, this reactivity has led to several different applications such as sensing of 1 O 2 , the release of cytotoxic reactive oxygen species (ROS), and stimuli-responsive materials for drug delivery. The rational design of acenes in these chemically-responsive applications beyond organic optoelectronics requires an understanding of how chemical structure influences both the physical properties, such as quantum yield of emission, as well as the reactivity of acenes and their cycloadducts. Therefore, the objective of this review is to summarize how cycloaddition reactions of acenes have expanded their applications in different areas of materials chemistry, and in doing so inspire and inform the rational design of acene-based materials with applications beyond organic electronics. Although they are often detrimental in organic electronics, the cycloaddition reactions of acenes, especially with singlet oxygen, are useful in a range of responsive materials.