Fluoranthene and its π-extended diimides: Construction of new electron acceptors

Ishikawa, Hiroyuki; Katayama, Koji; Nishida, Jun‐ichi; Kitamura, Chitoshi; Kawase, Takeshi

doi:10.1016/j.tetlet.2018.09.012

Cited by 9 publications

(6 citation statements)

References 44 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Thus, CPONI derivatives are of great interest to construct low band-gap D-A conjugated polymers with promising electronic structure and optoelectronic properties. Nevertheless, literature reports on the synthesis, reactivity, and optoelectronic properties of diarylcyclopentadienone-fused naphthalimide derivatives are rarely seen (Ding et al, 2015; Ishikawa et al, 2018). To our knowledge, the CPONI-based polymers have not been reported.…”

Section: Introductionmentioning

confidence: 99%

Low Bandgap Donor-Acceptor π-Conjugated Polymers From Diarylcyclopentadienone-Fused Naphthalimides

Guo

Yang

et al. 2019

Front. Chem.

View full text Add to dashboard Cite

Two novel aromatic imides, diarylcyclopentadienone-fused naphthalimides (BCPONI-2Br and TCPONI-2Br), are designed and synthesized by condensation coupling cyclopentadienone derivatives at the lateral position of naphthalimide skeleton. It has been found that BCPONI-2Br and TCPONI-2Br are highly electron-withdrawing acceptor moieties, which possess broad absorption bands and very low-lying LUMO energy levels, as low as −4.02 eV. On the basis of both building blocks, six low bandgap D-A copolymers (P1–P6) are prepared via Suzuki or Stille coupling reactions. The optical and electrochemical properties of the polymers are fine-tuned by the variations of donors (carbazole, benzodithiophene, and dithienopyrrole) and π-conjugation linkers (thiophene and benzene). All polymers exhibit several attractive photophysical and electrochemical properties, i.e., broad near-infrared (NIR) absorption, deep-lying LUMO levels (between −3.88 and −3.76 eV), and a very small optical bandgap as low as 0.81 eV, which represents the first aromatic diimide-based polymer with an of <1.0 eV. An investigation of charge carrier transport properties shows that P5 exhibits a moderately high hole mobility of 0.02 cm 2 V −1 s −1 in bottom-gate field-effect transistors (FETs) and a typical ambipolar transport behavior in top-gate FETs. The findings suggest that BCPONI-2Br, TCPONI-2Br, and the other similar acceptor units are promising building blocks for novel organic semiconductors with outstanding NIR activity, high electron affinity, and low bandgap, which can be extended to various next-generation optoelectronic devices.

show abstract

Section: Introductionmentioning

confidence: 99%

Low Bandgap Donor-Acceptor π-Conjugated Polymers From Diarylcyclopentadienone-Fused Naphthalimides

Guo

Yang

et al. 2019

Front. Chem.

View full text Add to dashboard Cite

show abstract

“…Previously, a similar PAH diimide was reported by Kawase et al. In the current contribution, with a new synthesis route and varied side chains to improve solubility, the molecule is fully characterized [20] …”

Section: Resultsmentioning

confidence: 70%

“…In the current contribution, with a new synthesis route and varied side chains to improve solubility, the molecule is fully characterized. [20] The structures of 1 a/b are confirmed by 1 H and 13 C NMR, as well as high-resolution mass spectroscopy. Then, X-ray crystallographic analysis is conducted with a single crystal of Chemistry-A European Journal are arranged with a nearly perfect perpendicular orientation with respect to the PAH plane, owing to the steric repulsion by the two carbonyl groups.…”

Section: Resultsmentioning

confidence: 81%

Syntheses of Anthracene‐Centered Large PAH Diimides and Conjugated Polymers**

Shi

Yang

et al. 2022

Chemistry A European J

View full text Add to dashboard Cite

Polycyclic aromatic hydrocarbon (PAH) structures with suitable electron‐withdrawing groups are useful building blocks for developing optical and electron‐transporting materials. Here, we report the application of a double benzannulation process to the syntheses of PAH diimides with enlarged π‐frameworks featuring a central anthracene moiety. The preparations are realized by copper‐catalyzed [4+2] cycloaddition of ethynyl‐substituted aromatic dicarboximide to 2,5‐bis(phenylethynyl)terephthalaldehyde, followed by intramolecular photocyclization or direct arylation via Heck cross coupling. A central symmetric benzo[1,2‐k:4,5‐k′]‐bis(fluoranthene)‐3,4,12,13‐tetracarboxyl diimide (BFDI) is acquired, with the single crystal structure revealing its completely planar polycyclic skeleton. Such a shape‐persistent PAH expectedly exhibits a tendency to stack face‐to‐face and forms J‐aggregates. Moreover, BFDI can be difunctionalized site‐selectively at the reactive 9 and 10 positions of the anthracene unit and then applied to prepare conjugated polymers. When coupled with 1,4‐diketopyrrolo[3,4‐c]‐pyrrole (DPP) via thiophene and dithiophene linkers, two polymers with significantly broadened absorption bands extended to the near‐infrared regime are obtained, evidencing the effective π‐conjugative extension ability of BFDI unit.

show abstract

“…This observation demonstrates that the corresponding azomethine ylide 7a is generated as a reactive intermediate by Et 3 N induced deprotonation of 8a. Additionally, reaction of 7a with the as a versatile synthetic intermediate [16][17][18][19] N-(2-ethylhexyl) acenphthylene-5,6-dicarboxylimide 11 was examined. Under similar conditions, this reaction produces the corresponding cycloadduct 12 in 31% yield ( Fig.…”

Section: Resultsmentioning

confidence: 99%

Isolation and characterisation of a stable 2-azaphenalenyl azomethine ylide

et al. 2019

Self Cite

View full text Add to dashboard Cite

Although azomethine ylides have been fully exploited as versatile reactive intermediates in dipolar cycloaddition reactions to construct a variety of heterocyclic compounds involving a nitrogen atom, little is known about their structural and electronic properties. Here a method is developed for the preparation, isolation and characterization of a stable 2-azaphenalenyl based azomethine ylide. N-Phenyl-5,8-di-t-butyl-2-azaphenalenyl cannot be isolated because it undergoes rapid dimerization by CC bond formation at the 1 and 3 positions. In contrast, sterically bulkier N-2,6-di(isopropyl)phenyl-5,8-di-t-butyl-2-azaphenalenyl can be generated and isolated as deep green crystals under deoxygenated conditions. X-ray crystal analysis of this stable azomethine ylide reveals that its azaphenalenyl skeleton has very small bond alternation and structural deformation. The results of spectroscopic and electrochemical theoretical studies indicate that N-2,6-di(isopropyl)phenyl-5,8-di-t-butyl-2-azaphenalenyl has electronic features that are similar to those of phenalenyl anion and it possesses an extremely high HOMO energy.

show abstract

Fluoranthene and its π-extended diimides: Construction of new electron acceptors

Cited by 9 publications

References 44 publications

Low Bandgap Donor-Acceptor π-Conjugated Polymers From Diarylcyclopentadienone-Fused Naphthalimides

Low Bandgap Donor-Acceptor π-Conjugated Polymers From Diarylcyclopentadienone-Fused Naphthalimides

Syntheses of Anthracene‐Centered Large PAH Diimides and Conjugated Polymers**

Isolation and characterisation of a stable 2-azaphenalenyl azomethine ylide

Contact Info

Product

Resources

About