Development of novel synthetic routes to bis(perfluoroalkyl)-substituted anthracene derivatives

Yamada, Shigeyuki; Kinoshita, Keiji; Iwama, Shota; Yamazaki, Takashi; Kubota, Toshio; Yajima, Tomoko

doi:10.1039/c3ra40974k

Cited by 17 publications

(21 citation statements)

References 28 publications

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“…PAH(R F ) n EAs increase significantlya nd uniformlya st he R F chains are lengthened Figure 1s hows that the EAs of NAPH(R F ) 4 and CORA(R F ) 5 increase monotonically as R F is lengthened from CF 3 to C 4 F 9 .T he EA differenceb etween CORA(CF 3 ) 5 and CORA(C 2 F 5 ) 5 is 0.145 eV (the DFT value is 0.13 eV). This is as ignificant change as far as these compounds acting as electron acceptors is concerned.…”

Section: Experimental and Computational Resultsmentioning

confidence: 93%

“…Absolute andr elative experimental EAs, experimental E 1/2 (0/À) values, and DFT-predicted absolutea nd relative EAs for ANTH, NAPH,N APH(R F ) 4 ,C ORA, CORA(R F ) 5 ,A NTH(CF 3 ) 6 ,a nd 1,7-C 60 (R F ) 2 [21] are listed in Ta ble S1 (R F = CF 3 ,C 2 F 5 , n-C 3 F 7 (hereinafter C 3 F 7 ), and n-C 4 F 9 (hereinafter C 4 F 9 )). Plots of the relative experimentala nd DFT EAs for NAPH(R F ) 4 and CORA(R F ) 5 are shown in Figure 1.…”

Section: Experimental and Computational Resultsmentioning

confidence: 99%

“…Table S1 also lists DFT EAs for 1,5‐NAPH(R F ) 2 , 1,5‐, 2,6‐, and 9,10‐ANTH(R F ) 2 , 2,6‐dihydroanthracene (2,6‐H 2 ‐ANTH), 2,6‐H 2 ‐1,5‐ANTH(R F ) 2 , 2,6‐H 2 ‐2,6‐ANTH(R F ) 2 , 2,3,6,7,9,20‐ANTH(R F ) 6 (R F =CF 3 , C 2 F 5 , C 3 F 7 , C 4 F 9 ), 1,5‐ and 2,6‐ANTH(F) 2 , 2,6‐H 2 ‐1,5‐ANTH(F) 2 , and 2,6‐H 2 ‐2,6‐ANTH(F) 2 . (Note that 9,10‐ANTH(CF 3 ) 2 is a known compound, but its electronic properties have not been reported …”

Section: Resultsmentioning

confidence: 99%

“…( Note that 9,10-ANTH(CF 3 ) 2 is ak nown compound, but its electronic properties have not been reported. [5] )T able S2 (Supporting Information) lists absolute and relative DFT EAs for CORA(R F ) 1-5 derivatives. Plots of some of these absolute and relative DFT EAs are shown in The gas-phase EA of am olecule is, by definition, its intrinsic ability to act as an electron acceptor.…”

Section: Experimental and Computational Resultsmentioning

confidence: 99%

“…n-Perfluoroalkyl groups are an importants eries of homologous substituents for both organic [1][2][3][4][5][6] and inorganic compounds. [7][8][9][10][11] The number of carbon atoms in these straight-chain substituents commonly varies from 1t o8by single integers.…”

Section: Introductionmentioning

confidence: 99%

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Experimental and DFT Studies of the Electron‐Withdrawing Ability of Perfluoroalkyl (R_F) Groups: Electron Affinities of PAH(R_F)_n Increase Significantly with Increasing R_F Chain Length

San

Spisak

Dubceac

et al. 2017

Chemistry A European J

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Two series of aromatic compounds with perfluoroalkyl (R ) groups of increasing length, 1,3,5,7-naphthalene(R ) and 1,3,5,7,9-corannulene(R ) , have been prepared and their electronic properties studied by low-temperature photoelectron spectroscopy (PES) (for gas-phase electron affinity measurements). These and many related compounds were also studied by DFT calculations. The data demonstrate unambiguously that the electron-withdrawing ability of R substituents increases significantly and uniformly from CF to C F to n-C F to n-C F .

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Section: Experimental and Computational Resultsmentioning

confidence: 93%

Section: Experimental and Computational Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Experimental and Computational Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Experimental and DFT Studies of the Electron‐Withdrawing Ability of Perfluoroalkyl (R_F) Groups: Electron Affinities of PAH(R_F)_n Increase Significantly with Increasing R_F Chain Length

San

Spisak

Dubceac

et al. 2017

Chemistry A European J

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Nucleophilic Additions of Perfluoroalkyl Groups

Beier

Zibinsky²,

Prakash

2016

Organic Reactions

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The trifluoromethyl and perfluoroalkyl functional groups possess significant thermal, chemical, and metabolic stability, as well as high lipophilicity and electronegativity. These physicochemical properties render fluorinated carbon residues indispensable in diverse applications, such as agrochemistry, drug design, and material chemistry. The generation and properties of nucleophilic perfluoroalkyl reagents as well as the scope and limitations of their additions to various electrophilic partners is described in this chapter.

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Efficient Syntheses of Novel Fluoro‐Substituted Pentacenes and Azapentacenes: Molecular and Solid‐State Properties

Schwaben

Münster

Klues

et al. 2015

Chemistry A European J

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Non-symmetrical 6,13-disubstituted pentacenes bearing trifluoromethyl and aryl substituents have been synthesized starting from pentacenequinone. Diazapentacenes with a variety of fluorine substituents were prepared either via a Hartwig-Buchwald aryl amination route or by a SNAr strategy. As a result of a non-symmetric substitution pattern containing electron-donating substituents in combination with electron-accepting fluorine substituents, the synthesized compounds feature distinct molecular dipoles. All compounds are analyzed regarding their optoelectronic properties in solution with special focus on the frontier orbital energies as well as their molecular packing in the crystal structures. The analyses of isolated molecules are complemented by thin-film studies to examine their solid-state properties. A precise comparison between these and the molecular properties gave detailed insights into the exciton binding energies of these compounds, which are explained by means of a simple model considering the molecular packing and polarizabilities.

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Development of novel synthetic routes to bis(perfluoroalkyl)-substituted anthracene derivatives

Cited by 17 publications

References 28 publications

Experimental and DFT Studies of the Electron‐Withdrawing Ability of Perfluoroalkyl (R_F) Groups: Electron Affinities of PAH(R_F)_n Increase Significantly with Increasing R_F Chain Length

Experimental and DFT Studies of the Electron‐Withdrawing Ability of Perfluoroalkyl (R_F) Groups: Electron Affinities of PAH(R_F)_n Increase Significantly with Increasing R_F Chain Length

Nucleophilic Additions of Perfluoroalkyl Groups

Efficient Syntheses of Novel Fluoro‐Substituted Pentacenes and Azapentacenes: Molecular and Solid‐State Properties

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Development of novel synthetic routes to bis(perfluoroalkyl)-substituted anthracene derivatives

Cited by 17 publications

References 28 publications

Experimental and DFT Studies of the Electron‐Withdrawing Ability of Perfluoroalkyl (RF) Groups: Electron Affinities of PAH(RF)n Increase Significantly with Increasing RF Chain Length

Experimental and DFT Studies of the Electron‐Withdrawing Ability of Perfluoroalkyl (RF) Groups: Electron Affinities of PAH(RF)n Increase Significantly with Increasing RF Chain Length

Nucleophilic Additions of Perfluoroalkyl Groups

Efficient Syntheses of Novel Fluoro‐Substituted Pentacenes and Azapentacenes: Molecular and Solid‐State Properties

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Product

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Experimental and DFT Studies of the Electron‐Withdrawing Ability of Perfluoroalkyl (R_F) Groups: Electron Affinities of PAH(R_F)_n Increase Significantly with Increasing R_F Chain Length

Experimental and DFT Studies of the Electron‐Withdrawing Ability of Perfluoroalkyl (R_F) Groups: Electron Affinities of PAH(R_F)_n Increase Significantly with Increasing R_F Chain Length