4,5,9,10‐Pyrene Diimides: A Family of Aromatic Diimides Exhibiting High Electron Mobility and Two‐Photon Excited Emission

Abstract

The design and synthesis of high-performance n-type organic semiconductors are important for the development of future organic optoelectronics. Facile synthetic routes to reach the K-region of pyrene and produce 4,5,9,10-pyrene diimide (PyDI) derivatives are reported. The PyDI derivatives exhibited efficient electron transport properties, with the highest electron mobility of up to 3.08 cm V s . The tert-butyl-substituted compounds (t-PyDI) also showed good one- and two-photon excited fluorescence properties. The PyDI derivatives are a new family of aromatic diimides that may exhibit both high electron mobility and good light-emitting properties, thus making them excellent candidates for future optoelectronics.

Organic Semiconductor Single Crystals for Electronics and Photonics

“…DBP thin films demonstrate a mobility of 0.21 cm 2 V −1 s −1 and blue emission with a PLQY of 47%; 1,6‐PyE thin films demonstrate a mobility of 0.17 cm 2 V −1 s −1 and 1,6‐PyE single crystals demonstrate yellow‐green emission with a PLQY of 28.8%; and 2,7‐PyE thin films demonstrate a mobility of 1.66 cm 2 V −1 s −1 and 2,7‐PyE single crystals demonstrate blue emission with a PLQY of 27.4%. More recently, Wu et al designed and synthesized a new series of pyrene derivatives, 4,5,9,10‐pyrenediimide (PyDI) derivatives, and found that the compound substituted with an n ‐pentyl moiety, C 5 ‐PyDI, exhibited efficient electron‐transport properties, with the highest electron mobility of 3.8 cm 2 V −1 s −1 , while its tert ‐butyl‐substituted compound, t‐C5‐PyDI, showed good two‐photon excited fluorescence properties . The chemical structures of the high‐mobility emissive anthracene and pyrene derivatives discussed above are shown in Scheme .…”

Efficient solid-state emission and reversible mechanofluorochromism of a tetraphenylethene-pyrene-based β-diketonate boron complex

“…Compounds 3 and 5 were synthesized according to the literatures. 25,28 The synthetic routes for b-diketonate boron complex BF 2 -TP were shown in Scheme 2. Firstly, the tetraphenylethene derivative 3 was synthesized by Suzuki-Miyaura coupling between 1 and boric acid 2.…”

Planar, Stair‐Stepped, and Twisted: Modulating Structure and Photophysics in Pyrene‐ and Benzene‐Fused N‐Heterocyclic Boranes

“…[10] Elemental analyses were performed on aP erkin-Elmer 2400 Series II analyzer.S imilarly to other reported fused-NHBs, [10] we were unable to obtain C,H,N-values for 3, 4, 8,a nd 11 due to air-and moisture-sensitivity.A ll chemicals were purchased from commercial sources and used directly unless noted otherwise. The 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPr•HCl), [34] 4,5,9,10-tetrabromo-2,7-ditert-butylpyrene, [35] and compound 1 [22][23] were prepared according to the literature procedures.…”