Tetra(peri‐naphthylene)anthracene: A Near‐IR Fluorophore with Four‐Stage Amphoteric Redox Properties

Abstract

A novel, benign synthetic strategy towards soluble tetra(peri-naphthylene)anthracene (TPNA) decorated with triisopropylsilylethynyl substituents has been established. The compound is perfectly stable under ambient conditions in air and features intense and strongly bathochromically shifted UV/vis absorption and emission bands reaching to near-IR region beyond 900 nm. Cyclic voltammetry measurements revealed four facilitated reversible redox events comprising two oxidations and two reductions. These remarkable experimental findings were corroborated by theoretical studies to identify the TPNA platform a particularly useful candidate for the development of functional near-IR fluorophores upon appropriate functionalization.

On‐Surface Synthesis of Non‐Benzenoid Nanographenes Embedding Azulene and Stone‐Wales Topologies

“…[12] Nevertheless, one of the main challenges limiting the study of non-benzenoid molecules is their difficult synthesis and separation, and only a few examples have been successfully reported. [9][10][11][13][14][15][16][17][18][19][20][21][22] In contrast, the "bottom-up" approach, combining modern solutions and on-surface syntheses to create NGs with atomically precise edge structures, has recently appeared as an alternative. [23] Over the last decade, the field of on-surface chemistry has experienced a great progress, with the successful achievement of a plethora of advanced metal-catalyzed onsurface reactions unattainable through solution chemistry.…”

“…Nevertheless, one of the main challenges limiting the study of non‐benzenoid molecules is their difficult synthesis and separation, and only a few examples have been successfully reported [9–11,13–22] . In contrast, the “bottom‐up” approach, combining modern solutions and on‐surface syntheses to create NGs with atomically precise edge structures, has recently appeared as an alternative [23] …”

Pyrene-bridged acenaphthenes: synthesis and properties of a diacenaphtho[1,2-e:1′,2′-l]pyrene and its symmetrical nitrogen analogue

“…3 The incorporation of cyclopenta-fused rings into the backbone is a promising method, since a cyclopentadienyl anion can be formed in such molecules. 4–6 A well-known building block in this context is acenaphthylene, which contains such a cyclopenta-annulated unit and has therefore already been employed in organic semiconductors, organic photovoltaics and organic light-emitting diodes. 1,5,7 Modification of the optoelectronic properties of acenaphthylene can be achieved by π-expansion as shown in Fig.…”

“…12 In addition, other π-expanded molecules consisting of acenaphthylene units are known in the literature. 4,13 Moreover, diacenaphthopyrene has already been theoretically investigated by Chao and Chen, who illustrated that diacenaphthopyrenes, containing electron withdrawing substituents or atoms, are potentially applicable as n-type materials. 14 Herein, we report the first synthesis of 8-( tert -butyl)diacenaphtho[1,2- e :1′,2′- l ]pyrene which represents, to the best of our knowledge, the first example of a previously unknown core structure (Scheme 1).…”