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How to Stabilize Large Soluble (Hetero-)Acenes

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Journal J Am Chem Soc
Specialty Chemistry
Date 2024 Jun 11
PMID 38862130
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Abstract

The higher acenes and azaacenes (>(aza)heptacenes) are fascinating, yet elusive materials. Their reactivity and sensitivity increases concomitantly with their size. In recent years, confinement techniques, that is isolation of acenes in matrices and on surfaces, has surpassed solution-based chemistry with respect to accessing the larger (hetero)acenes at the price of the accessibility of no more than a couple thousands of molecules. Isolating acenes in bulk quantities and in processable form is vital for applications in organic electronics as well as from a viewpoint from basic research. In this Perspective, we will discuss after a short historical outline their degradation pathways, and then will selectively highlight recent efforts in stabilizing soluble (aza)acenes.

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References
1.
Engelhart J, Lindner B, Tverskoy O, Rominger F, Bunz U . Partially fluorinated tetraazaacenes by nucleophilic aromatic substitution. J Org Chem. 2013; 78(21):10832-9. DOI: 10.1021/jo401824g. View

2.
Sola M . Forty years of Clar's aromatic π-sextet rule. Front Chem. 2014; 1:22. PMC: 3982536. DOI: 10.3389/fchem.2013.00022. View

3.
Miyazaki T, Watanabe M, Matsushima T, Chien C, Adachi C, Sun S . Heptacene: Synthesis and Its Hole-Transfer Property in Stable Thin Films. Chemistry. 2021; 27(41):10677-10684. DOI: 10.1002/chem.202100936. View

4.
Zong W, Hippchen N, Zeitter N, Maier S, Ludwig P, Rominger F . Stabilizing Azaheptacenes. J Am Chem Soc. 2024; 146(9):5793-5798. PMC: 10921409. DOI: 10.1021/jacs.3c13629. View

5.
Watanabe M, Chen K, Chang Y, Chow T . Acenes generated from precursors and their semiconducting properties. Acc Chem Res. 2013; 46(7):1606-15. DOI: 10.1021/ar400002y. View