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This paper intends to provide an overview for using corannulene derivatives in organic electronics such as organic field-effect transistors (OFETs), organic solar cells (OSCs), and organic light-emitting diodes (OLEDs). We highlight the rational design strategies, tuning molecular orbital energy levels and arrangement in single crystals of corannulenes. The topological structure and properties of corannulene make it a unique candidate for organic electronics. 相似文献
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《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2017,129(49):15766-15770
In the long history of corannulene chemistry, the 1,3‐dipolar cycloaddition to corannulene is unprecedented. Reported herein is the 1,3‐dipolar cycloaddition of a polycyclic aromatic azomethine ylide to corannulene, a reaction which occurs exclusively at the rim bond of corannulene, from the convex side in an exo fashion. The cycloadducts were successfully converted, by successive oxidative dehydrogenation, into pyrrole‐fused corannulenes, which exhibited pronounced solvatofluorochromism. 相似文献
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Zheng Zhou Zheng Wei Yuki Tokimaru Shingo Ito Kyoko Nozaki Marina A. Petrukhina 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2019,131(35):12235-12239
Mono‐ and dianions of 2‐tert‐butyl‐3a2‐azapentabenzo[bc,ef,hi,kl,no]corannulene ( 1 a ) were synthesized by chemical reduction with sodium and cesium metals, and crystallized as the corresponding salts in the presence of 18‐crown‐6 ether. X‐ray diffraction analysis of the sodium salt, [{Na+(18‐crown‐6)(THF)2}3{Na+(18‐crown‐6)(THF)}( 1 a 2?)2], revealed the presence of a naked dianion. In contrast, controlled reaction of 1 a with Cs allowed the isolation of singly and doubly reduced forms of 1 a , both forming π‐complexes with cesium ions in the solid state. In [{Cs+(18‐crown‐6)}( 1 a ?)]?THF, asymmetric binding of the Cs+ ion to the concave surface of 1 a ? is observed, whereas in [{Cs+(18‐crown‐6)}2( 1 a 2?)], two Cs+ ions bind to both the concave and convex surfaces of the dianion. The present study provides the first successful isolation and characterization of the reduced products of heteroatom‐containing buckybowl molecules. 相似文献
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Martin Chin 《European Polymer Journal》2007,43(5):2165-2169
Modified corannulene based transition metal complexes of titanium as a novel group of metallocene catalysts were synthesized and investigated in coordination polymerization reactions as catalysts in the syndiospecific bulk polymerization of styrene. In comparison to the zirconium complex exo-(η5-C20H17)(η5-C5H5)ZrCl2, the titanium complex η5-C20H17Ti(OiPr)3 shows a significantly increased polymerization activity, a considerably improved stereoregularity of the syndiotactic polymer chain, indicated by the increased melting temperature of 269 °C, as well as a higher weight average molecular weight and a narrower molecular weight distribution. 相似文献
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Changfeng Si Tao Wang Abhishek Kumar Gupta David B. Cordes Alexandra M. Z. Slawin Jay S. Siegel Eli Zysman-Colman 《Angewandte Chemie (International ed. in English)》2023,62(43):e202309718
Corannulene-derived materials have been extensively explored in energy storage and solar cells, however, are rarely documented as emitters in light-emitting sensors and organic light-emitting diodes (OLEDs), due to low exciton utilization. Here, we report a family of multi-donor and acceptor (multi-D-A) motifs, TCzPhCor, TDMACPhCor, and TPXZPhCor, using corannulene as the acceptor and carbazole (Cz), 9,10-dihydro-9,10-dimethylacridine (DMAC), and phenoxazine (PXZ) as the donor, respectively. By decorating corannulene with different donors, multiple phosphorescence is realized. Theoretical and photophysical investigations reveal that TCzPhCor shows room-temperature phosphorescence (RTP) from the lowest-lying T1; however, for TDMACPhCor, dual RTP originating from a higher-lying T1 (T1H) and a lower-lying T1 (T1L) can be observed, while for TPXZPhCor, T1H-dominated RTP occurs resulting from a stabilized high-energy T1 geometry. Benefiting from the high-temperature sensitivity of TPXZPhCor, high color-resolution temperature sensing is achieved. Besides, due to degenerate S1 and T1H states of TPXZPhCor, the first corannulene-based solution-processed afterglow OLEDs is investigated. The afterglow OLED with TPXZPhCor shows a maximum external quantum efficiency (EQEmax) and a luminance (Lmax) of 3.3 % and 5167 cd m−2, respectively, which is one of the most efficient afterglow RTP OLEDs reported to date. 相似文献