ChemInform Abstract: Synthesis and Structural Characterization of Boron Subphthalocyaninates.

Potz, Roland; Goeldner, Melanie; Hueckstaedt, Heiner; Cornelissen, Ursula; Tutaß, Andreas; Homborg, H.

doi:10.1002/chin.200016159

Cited by 4 publications

(11 citation statements)

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“…In our hands, the synthesis of Br-BsubPc as described by Potz et al 4 was found to be successful after some adaptations. The process is similar to that used for Cl-BsubPc in that it starts by dissolving phthalonitrile in solvent and adding a boron trihalide (in this case neat BBr 3 , Scheme 1).…”

Section: Resultsmentioning

confidence: 62%

“…The saturated solution was then sampled, passed through a GS-Tek PTFE 13 mm 0.22 μm syringe filter, and serially diluted until the absorbance fell within the linear range of the spectrometer. The absorption spectrum 4 as follows: In a 100 mL three-neck round bottomed flask, equipped with a magnetic stir-bar, a gas inlet, a condenser, and two rubber sleeve stoppers, phthalonitrile (4.0 g, 0.0312 mol) was dissolved in a 3:1 mixture of toluene−bromobenzene (50 mL). The vessel was kept under an inert atmosphere of argon, and a syringe and needle were used to slowly add boron tribromide (0.96 mL, 0.010 mol) to the solution.…”

Section: Introductionmentioning

confidence: 99%

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Crystal Structures, Reaction Rates, and Selected Physical Properties of Halo-Boronsubphthalocyanines (Halo = Fluoride, Chloride, and Bromide)

et al. 2012

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The physical properties, including the solid state arrangement, photophysics, solubility, and electrochemical behavior of a series of halo-BsubPcs (halo = F, Cl, Br) have been measured (IUPAC name halo-(7,12:14,19-diimino-21,5-nitrilo-5H-tribenzo(c,h,m)(1,6,11)triazacyclopentadecinato)-boron(III)). We have found that across the series all are relatively similar in most regards. Exceptions include that F-BsubPc can be 5 to 25 times more soluble than Cl-BsubPc in common organic solvents. F-BsubPc was also found to be hydrolytically stable under the conditions tested, whereas Cl-BsubPc and Br-BsubPc readily hydrolyzed to form HO-BsubPc. The relative rates of reaction for the series of halo-BsubPcs under standard phenoxylation conditions have also been measured. It was found that F-BsubPc does not undergo phenoxylation, whereas Br-BsubPc showed a markedly higher reaction rate relative to Cl-BsubPc. Based on these data some assumptions can be made as to the suitability of either F-BsubPc or Br-BsubPc to be used in place of the more common Cl-BsubPc. The data indicate that F-BsubPc is a potential replacement for Cl-BsubPc in organic electronic materials whereas Br-BsubPc might be more suitable as a chemical intermediate. Comments on the synthetic methods used to produce each halo-BsubPc are also made.

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Section: Resultsmentioning

confidence: 62%

Section: Introductionmentioning

confidence: 99%

Crystal Structures, Reaction Rates, and Selected Physical Properties of Halo-Boronsubphthalocyanines (Halo = Fluoride, Chloride, and Bromide)

et al. 2012

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“…3-Methylphenoxy-Boron Subphthalocyanine (3-MePhO-BsubPc, 8). Br-BsubPc was prepared based on the method previously reported 44 by modifying a published procedure by Potz et al 32 A similar procedure to the one previously described by Paton et al was followed. 17 Br-BsubPc was used as a starting material instead of Cl-BsubPc to decrease the reaction time.…”

Section: ■ Introductionmentioning

confidence: 99%

A Comprehensive Scope of Peripheral and Axial Substituent Effect on the Spectroelectrochemistry of Boron Subphthalocyanines

et al. 2018

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An extensive study of the electrochemical and spectroelectrochemical properties of 14 boron subphthalocyanine (BsubPc) derivatives with various axial and peripheral substituents was performed in 1,2-dichloromethane (CHCl) containing 0.1 M tetra- n-butyl-ammonium perchlorate (TBAP) as the supporting electrolyte. From the cyclic voltammetry results, all compounds exhibit one oxidation and at least two reduction processes within the solvent potential window of +1.6 to -1.8 V vs SCE. It was found that the reversibility of the redox reactions depends on the axial and peripheral substituents and the dipole moment of the boron-to-axial substituent. In general, UV-vis absorption spectra of the singly reduced BsubPc derivatives exhibit three equal intensity peaks in the 450 to 650 nm region that are derived from the maximum BsubPc absorbance peak upon reduction. Axial substituents affect the intensity of the three peaks upon reduction, while peripheral substituents shift the position of the peaks to higher wavelengths. Upon oxidation, the UV-vis absorption profile flattens considerably with only a single broad (∼300 nm) band apparent. Understanding the effect of substituents on the stability of the redox processes of BsubPcs will aid in further development of these materials for applications in organic electronic devices.

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“…It is in fact known that the axial boron-chloride bond is labile already in the presence of moderate nucleophiles in solution. 52 Also, dechlorination is a known process for instance in the case of iron octaethylporphyrin chloride (FeCl-OEP) on Cu(111) 45 and Au(III)-tetraphenylporphyrin chloride ([Au III TPP] + Cl – ) on Au (111). 44 Note that at least in the case of FeCl-OEP on Cu(111) chlorine adatoms were not clearly visible either.…”

Section: Resultsmentioning

confidence: 99%

Sticking with the Pointy End? Molecular Configuration of Chloro Boron-Subphthalocyanine on Cu(111)

et al. 2016

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In this combined low-temperature scanning tunneling microscopy (STM) and density functional theory (DFT) study, we investigate self-assembly of the dipolar nonplanar organic semiconductor chloro boron-subphthalocyanine (ClB-SubPc) on Cu(111). We observe multiple distinct adsorption configurations and demonstrate that these can only be understood by taking surface-catalyzed dechlorination into account. A detailed investigation of possible adsorption configurations and the comparison of experimental and computational STM images demonstrates that the configurations correspond to “Cl-up” molecules with the B–Cl moiety pointing toward the vacuum side of the interface, and dechlorinated molecules. In contrast to the standard interpretation of adsorption of nonplanar molecules in the phthalocyanine family, we find no evidence for “Cl-down” molecules where the B–Cl moiety would be pointing toward the Cu surface. We show computationally that such a configuration is unstable and thus is highly unlikely to occur for ClB-SubPc on Cu(111). Using these assignments, we discuss the different self-assembly motifs in the submonolayer coverage regime. The combination of DFT and STM is essential to gain a full atomistic understanding of the surface–molecule interactions, and our findings imply that phthalocyanines may undergo surface-catalyzed reactions hitherto not considered. Our results also indicate that care has to be taken when analyzing possible adsorption configurations of polar members of the phthalocyanine family, especially when they are adsorbed on comparably reactive surfaces like Cu(111).

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ChemInform Abstract: Synthesis and Structural Characterization of Boron Subphthalocyaninates.

Cited by 4 publications

References 1 publication

Crystal Structures, Reaction Rates, and Selected Physical Properties of Halo-Boronsubphthalocyanines (Halo = Fluoride, Chloride, and Bromide)

Crystal Structures, Reaction Rates, and Selected Physical Properties of Halo-Boronsubphthalocyanines (Halo = Fluoride, Chloride, and Bromide)

A Comprehensive Scope of Peripheral and Axial Substituent Effect on the Spectroelectrochemistry of Boron Subphthalocyanines

Sticking with the Pointy End? Molecular Configuration of Chloro Boron-Subphthalocyanine on Cu(111)

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