Octupolar Polycyclic Aromatic Hydrocarbons as New Two‐Photon Absorption Chromophores: Synthesis and Application for Optical Power Limiting

Zeng, Zebing; Guan, Zhuo; Xu, Qing‐Hua; Wu, Jishan

doi:10.1002/chem.201003235

Cited by 33 publications

(26 citation statements)

References 40 publications

(39 reference statements)

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“…Hexaphenylbenzenes (HPBs) and their oxidized derivatives hexa‐ peri ‐hexabenzocoronenes (HBCs) have received tremendous attention during the past 20 years in materials chemistry, for example in molecular electronics and nonlinear optics . They have proven to be a suitable scaffold for catalytic applications, the design of supramolecular architectures, as well as a perfectly sized template for the preparation of nano‐ring and nano‐ball structures.…”

Section: Introductionmentioning

confidence: 99%

Multiple‐Porphyrin Functionalized Hexabenzocoronenes

Martin

Lungerich

Hampel

et al. 2019

Chemistry A European J

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Porphyrin–hexabenzocoronene architectures serve as good model compounds to study light‐harvesting systems. Herein, the synthesis of porphyrin functionalized hexa‐peri‐hexabenzocoronenes (HBCs), in which one or more porphyrins are covalently linked to a central HBC core, is presented. A series of hexaphenylbenzenes (HPBs) was prepared and reacted under oxidative coupling conditions. The transformation to the respective HBC derivatives worked well with mono‐ and tri‐porphyrin‐substituted HPBs. However, if more porphyrins are attached to the HPB core, Scholl oxidations are hampered or completely suppressed. Hence, a change of the synthetic strategy was necessary to first preform the HBC core, followed by the introduction of the porphyrins. All products were fully characterized, including, if possible, single‐crystal XRD. UV/Vis absorption spectra of porphyrin‐HBCs showed, depending on the number of porphyrins as well as with respect to the substitution pattern, variations in their spectral features with strong distortions of the porphyrins’ B‐band.

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Section: Introductionmentioning

confidence: 99%

Multiple‐Porphyrin Functionalized Hexabenzocoronenes

Martin

Lungerich

Hampel

et al. 2019

Chemistry A European J

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“…The scope of the Scholl-type reaction with HPB precursors ranges from the preparation of insoluble unsubstituted, hexakis-halides (I, F) HBCs [25,26] to soluble derivatives carrying alkyl (chiral, linear, branched), alkylphenyl, iodophenyl, or mono/multiple bromide [5], iodofluorenes [27], methylene iodide [28], and heteroaromatics [29] on the periphery. Tris(biphenyl)benzene substrates were transformed to the corresponding trialkyl [30], hexakis-alkoxy [18], or triiodo [19] HBCs.…”

Section: Synthesis Of Hbc and Its Derivativesmentioning

confidence: 99%

“…In general, electron-withdrawing (as nitriles or carbonyls) or donor (as alkoxy or amines) substituents hinder the planarization reaction [28]. However, introduction of spacers or additional peripheral substituents, which counteract the undesired electronic effect, can improve the outcome of the reaction.…”

Section: Synthesis Of Hbc and Its Derivativesmentioning

confidence: 99%

“…Star-shaped HBC 24 [59] and C3-symmertric "octupolar" HBC 25 [28] have been reported as attractive target molecules for two-photon absorption owing to their donor-acceptor characteristics. Six-fold symmetric compound 24 was prepared from the cyclized hexaiodo counterpart and subsequent attachment of the fully conjugated peripherial acceptors via Pd-catalyzed Heck reaction.…”

Section: Synthesis Of Hbc and Its Derivativesmentioning

confidence: 99%

“…Alternating donor and acceptor substituents in compound 25 were elegantly introduced starting with an asym metric tolane carrying alkoxys and ester functionalities. From a triphosphonate HBC intermediate, nitro-, nitrile-, and trifluoromethyl were installed by Wittig-Wadsworth-Emmons reaction [28].…”

Section: Synthesis Of Hbc and Its Derivativesmentioning

confidence: 99%

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Hexa-peri-hexabenzocoronene in organic electronics

Seyler

Purushothaman

Jones

et al. 2012

Pure and Applied Chemistry

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Polycyclic aromatic hydrocarbons (PAHs) are in a class of functional organic compounds with increasing importance in organic electronics. Their tunable photophysical properties and typically strong intermolecular associations make them ideal materials in applications where control of charge mobility is essential. Hexa-peri-hexabenzocoronene (HBC) is a disc-shaped PAH that self-associates into columnar stacks through strong π-π interactions. By decorating the periphery of the HBC molecule with various substituents, a range of properties and functions can be obtained including solution processability, liquid crystallinity, and semiconductivity. In this review article, the synthesis, properties, and functions of HBC derivatives are presented with focus on work published in the last five years.

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Synthesis, Photophysics, and Electronic Structures of Benzene‐Linked Bispyrimidine Compounds

Song

Liu

et al. 2015

Asian J Org Chem

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Seven multi‐dipole and multibranched benzene‐linked bispyrimidine derivatives containing a two‐layer binary tree structure with different electron donor and acceptor groups were designed, synthesized, and characterized. The influences of substituents and solvents on the optical properties of the compounds were investigated. The UV/vis absorption (λabsmax: 311–371 nm), PL emission (λemmax: 386–527 nm), stokes shift (2864–6414 cm−1), and fluorescence quantum yield (Φf: 0.01∼0.16) of the compounds in CH3CN solution are influenced by the electron‐donor or accept substituents. The absorption and emission spectra of the compound with the highest Φf in various solvents indicate that the solvent has little influence on absorption spectrum but does influence the emission spectrum. Transient absorption spectra exhibiting strong positive absorption bands in the near‐IR wavelength means that these compounds could potentially be used as optical limiting materials, which is further confirmed by the quantum chemical calculations.

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Octupolar Polycyclic Aromatic Hydrocarbons as New Two‐Photon Absorption Chromophores: Synthesis and Application for Optical Power Limiting

Abstract: Bigger is better! Large‐size octupolar polycyclic aromatic hydrocarbons can be used as new two‐photon absorption (TPA) chromophores with large TPA cross sections for optical power limiting (see graphic).

Cited by 33 publications

References 40 publications

Multiple‐Porphyrin Functionalized Hexabenzocoronenes

Multiple‐Porphyrin Functionalized Hexabenzocoronenes

Hexa-peri-hexabenzocoronene in organic electronics

Synthesis, Photophysics, and Electronic Structures of Benzene‐Linked Bispyrimidine Compounds

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