Acenaphthylene as a building block for π-electron functional materials

Liu, Ying-Hsuan; Perepichka, Dmitrii F.

doi:10.1039/d1tc02826j

Cited by 38 publications

(24 citation statements)

References 131 publications

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“…[2,6] Hence, the incorporation of πconjugated cyclopentadiene moieties, which are prone to facilitated electron uptake driven by the aromaticity gain, resulted in highly interesting electron-deficient systems. [3,7] By this approach not only the electron affinity of the PAH scaffold increases but also its geometry can efficiently be modulated towards curved systems, [8] which, in turn, has a pronounced effect on aggregation behavior and reactivity. [2,9] Pyracylene (cyclopenta[fg]acenaphthylene, 1), initially reported back in the late 1960s, [10] can be considered as a paradigmatic example of an electron-accepting PAH comprising 5-membered rings (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

“…The incorporation of nonbenzenoid rings into the sp 2 ‐carbon framework is a particularly attractive concept to endow PAHs with electron acceptor properties and non‐planarity [2,6] . Hence, the incorporation of π‐conjugated cyclopentadiene moieties, which are prone to facilitated electron uptake driven by the aromaticity gain, resulted in highly interesting electron‐deficient systems [3,7] . By this approach not only the electron affinity of the PAH scaffold increases but also its geometry can efficiently be modulated towards curved systems, [8] which, in turn, has a pronounced effect on aggregation behavior and reactivity [2,9] …”

Section: Introductionmentioning

confidence: 99%

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Inducing Curvature to Pyracylene upon π‐Expansion

Bergner

Walla

Röminger

et al. 2022

Chemistry A European J

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We disclose a successive π‐expansion of pyracylene towards boat‐shaped polycyclic scaffolds. The unique structural features of the resulting compounds were revealed by X‐ray crystallographic analysis. Depending on the extent of π‐expansion the compounds display intense bathochromically shifted absorption bands in their UV/Vis spectra and are prone to several redox events as documented by cyclic voltammetry. The experimental observations are in line with the computational studies based on density functional theory, suggesting progressive narrowing of the HOMO–LUMO gap and distinct evolution of the electronic structure and aromaticity.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Inducing Curvature to Pyracylene upon π‐Expansion

Bergner

Walla

Röminger

et al. 2022

Chemistry A European J

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“…Moreover, it shows attractive electron-deficient feature because of the cyclopentene-fused nonalternant structure. [57][58][59] Currently, fluoranthene-based building blocks have been widely used for constructing organic semiconductors. [60][61][62][63] Among them diazabenzo[k]fluoranthene derivatives have attracted particular interests as a type of efficient A units for constructing NFAs and thermally activated delayed fluorescence emitters.…”

Section: Introductionmentioning

confidence: 99%

A New Diazabenzo[k]fluoranthene‐Based D‐A Conjugated Polymer Donor for Efficient Organic Solar Cells

Wang

Liu

et al. 2022

Macromol. Rapid Commun.

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The development of wide-bandgap polymer donors having complementary absorption and compatible energy levels with near-infrared (NIR) absorbing nonfullerene acceptors is highly important for realizing high-performance organic solar cells (OSCs). Herein, a new thiophene-fused diazabenzo[k]fluoranthene derivative is successfully synthesized as the electron-deficient unit to construct an efficient donor-acceptor (D-A) type alternating copolymer donor, namely, PABF-Cl, using the chlorinated benzo[1,2-b:4,5-b']dithiophene as the copolymerization unit. PABF-Cl exhibits a wide optical bandgap of 1.93 eV, a deep highest occupied molecular level of −5.36 eV, and efficient hole transport. As a result, OSCs with the best power conversion efficiency of 11.8% are successfully obtained by using PABF-Cl as the donor to blend with a NIR absorbing BTP-eC9 acceptor. This work provides a new design of electron-deficient unit for constructing high-performance D-A type polymer donors.

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“…Expansion of aromatic systems via peripheral fusion of acenaphthylene units has been recognized as an efficient strategy for development of organic semiconductors and chromophores [1–4] . Decacyclene ( DC , Figure 1), discovered by Rehländer and Dziewoński more than a century ago, [5, 6] may be viewed as an early prototype of such an acenaphthylene‐fused system.…”

Section: Introductionmentioning

confidence: 99%

Tridecacyclene Tetraimide: An Easily Reduced Cyclooctatetraene Derivative

et al. 2022

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Tridecacyclene tetraimide, TCTI, an electrondeficient non-benzenoid nanocarbon with a C 56 N 4 polycyclic framework was obtained in a concise synthesis. TCTI has a non-planar structure and forms π-stacked dimers in the solid state. In solution, it undergoes eight single-electron reductions, yielding a range of negatively charged states up to an octaanion. Except for the latter species, which has a remarkably large electronic gap, the anions feature extended near-infrared absorptions, with a particularly strong band at 1692 nm observed for the dianion. A computational analysis of the TCTI anions shows that their stability originates from the combined effects of electron-deficient imide groups and the local aromaticity of reduced acenaphthylene units. The properties of TCTI make it potentially useful in electrochromic and charge storage applications.

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Acenaphthylene as a building block for π-electron functional materials

Abstract: This is the first review paper focusing on acenaphthylene (AN), an important building block of many organic semiconductors. We summarize the most important literature on -conjugated AN derivatives, both small...

Cited by 38 publications

References 131 publications

Inducing Curvature to Pyracylene upon π‐Expansion

Inducing Curvature to Pyracylene upon π‐Expansion

A New Diazabenzo[k]fluoranthene‐Based D‐A Conjugated Polymer Donor for Efficient Organic Solar Cells

Tridecacyclene Tetraimide: An Easily Reduced Cyclooctatetraene Derivative

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