cis andtrans Forms of a Binuclear Subphthalocyanine

Fukuda, Takamitsu; Stork, Jay R.; Potucek, Richard J.; Olmstead, Marilyn M.; Noll, Bruce C.; Kobayashi, Nagao; Durfee, William S.

doi:10.1002/1521-3773(20020715)41:14<2565::aid-anie2565>3.0.co;2-g

Cited by 84 publications

(49 citation statements)

References 10 publications

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“…The second interaction is a organic compounds o462 centrosymmetric pair of convex-convex -stacked isoindoline units which links the ribbons of BsubPc molecules together. In contrast, the halo-F 12 BubPc motif is characterized by columns of BsubPc molecules oriented approximately perpendicular to the BsubPc molecular plane (Rodríguez-Morgade et al, 2008;Fukuda et al, 2002;. An example of this motif is shown by the crystal structure of Br-F 12 BsubPc in Fig.…”

Section: Figurementioning

confidence: 98%

“…These motifs are also consistent with peripherally fused or hybrid BsubPcs. For example, fluorinated BsubPc dimers joined peripherally through one isoindole unit in both the cis and trans forms crystallize according to the F 12 BsubPc motif (Fukuda et al, 2002). The crystal structure of the cis form shows columns of BsubPcs as the F 12 BsubPc motif would predict, with the other BsubPc of the dimer protruding from the stack and alternating in opposite directions with neighbouring molecules.…”

Section: Figurementioning

confidence: 99%

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Sulfonate pseudohalides of boron subphthalocyanine

2012

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The crystal structures of three sulfonate pseudohalide derivatives of boron subphthalocyanine (BsubPc) are described and compared with four structures of three published sulfonate derivatives. Benzenesulfonate boron subphthalocyanine [(benzenesulfonato)(subphthalocyaninato)boron, C(30)H(17)BN(6)O(3)S, (I)] crystallizes in the space group P-1 with Z = 2. The structure contains two centrosymmetric π-stacking interactions between the concave faces of the isoindoline units in the BsubPc ligands. 3-Nitrobenzenesulfonate boron subphthalocyanine [(3-nitrobenzenesulfonato)(subphthalocyaninato)boron, C(30)H(16)BN(7)O(5)S, (II)] crystallizes in the space group P2(1)/c with Z = 4. The structure contains an intermolecular S-O···π interaction from the sulfonate group to a five-membered N-containing ring of an isoindoline unit on the concave side of a neighbouring BsubPc ligand, at a distance of 3.151 (3) Å. The crystal of methanesulfonate boron subphthalocyanine [(methanesulfonato)(subphthalocyaninato)boron, C(25)H(15)BN(6)O(3)S, (III)] was produced via sublimation and it is not a solvate, in contrast with two previously published structures of the same compound. Compound (III) crystallizes in the space group P2(1)/n with Z = 2, and its structure is similar to that of the more common compound Cl-BsubPc.

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Section: Figurementioning

confidence: 98%

Section: Figurementioning

confidence: 99%

Sulfonate pseudohalides of boron subphthalocyanine

2012

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“…In addition, subphthalocyanine analogues with an extended p-system: (subphthalocyanines [22][23][24], subazaphenalenephthalocyanines [25] and planar bi-and trinuclear subphthalocyanines [26,27]), have been obtained and identified.…”

Section: Introductionmentioning

confidence: 99%

Subphthalocyanines as electron mediators in biosensors based on phenol oxidases: Application to the analysis of red wines

Gonzalez-Anton

Osipova

García-Hernández

et al. 2017

Electrochimica Acta

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The electron mediator properties of three subphthalocyanines (SubPcs) [hexa-chloro boron subphthalocyanine (ClSubPc), tri-tert-butyl boron subphthalocyanine (t-BuSubPc) and hexa-phenoxy boron subphthalocyanine (PhOSubPc)] in Tyrosinase and Laccase biosensors (deposited on ITO glass) for the detection of catechol and hydroquinone were evidenced. A particularly remarkable performance was observed in the PhOSubPc-Tyr sensor, which takes account of the p-p interactions between subphthalocyanine rings and the active sites of the enzymes. Mediated electron transfer between redox enzymes and the ITO electrode improved the limits of detection by one order of magnitude, reaching 10 À7 molÁL À1 values. Studies at increasing scan rates confirmed the improvement of the charge transfer rates caused by the presence of the SubPcs. A bioelectronic tongue formed by an array of the SubPc based biosensors has been able to discriminate red wines according to their Total Polyphenol Index.

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“…Initially, we anticipated that a SubPc-POP substituted with chlorine atoms in the axial position would exhibit a concave-to-ligand solid-state packing motif similar to the trans binuclear SubPc systems previously reported by Kobayashi and Durfee. 47 However, these polymeric systems could not be constructed due to the chemical instability of 1b.…”

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confidence: 99%