182575-04-8

Upstream product

• 182575-02-6 bromo-[7,12:14,19-diimino-21,5-nitrilo-5H-tribenzo[c,h,m][1,6,11]triazacyclopentadecinato-(2)-κN22,κN23,κN24]-boron(III) 
• 108-95-2 phenol 
• 10294-33-4 boron tribromide 
• 91-15-6 phthalonitrile 
• 36530-06-0 subphthalocyanine 
• 182561-76-8 hydroxy-[7,12:14,19-diimino-21,5-nitrilo-5H-tribenzo[c,h,m][1,6,11]triazacyclopentadecinato-(2)-κN22,κN23,κN24]-boron(III) 
• 1360624-39-0 4-toluenesulfonate-boronsubphthalocyanine 
• 1360624-41-4 (methanesulfonato)(subphthalocyaninato)boron 
• 1360624-43-6 (benzenesulfonato)(subphthalocyaninato)boron 
• 1360624-44-7 4-chlorobenzenesulfonate-boronsubphthalocyanine 
• 1360624-45-8 (3-nitrobenzenesulfonato)-(subphthalocyaninato)boron 
• 7446-70-0 aluminium trichloride 
• 10294-34-5 boron trichloride 
• 1529-17-5 phenyltrimethylsilyl ether 

Relevant academic research and scientific papers

Direct Access to Axially Substituted Subphthalocyanines from Trimethylsilyl-Protected Nucleophiles

A new synthetic one-step approach to perform the axial ligand exchange reaction in subphthalocyanines that employs trimethylsilyl-protected nucleophiles as starting materials is reported. Theoretical calculations indicate that the exchange reaction procee

Structure and some properties of (alkoxo)(subphthalocyaninato)boron(III)

A few (alkoxo)(subphthalocyaninato)boron(III) complexes, [BX(subpc) ] (X=OMe, OEt, OBu1, and OPh), were prepared and characterized. The molecular structure of [B(OEt)(subpc)] was determined by an X-ray structure analysis; the boron atom is situated 0.642 A upward from the triangle plane of three isoindoline nitrogen atoms. The geometry of the boron atom is distorted tetrahedral, and the complex shows a wine-glass shape. The mass spectra showed that a part of the hydrogen atoms of the subphthalocyanine ring are displaced by the halogen atoms of boron trihalide or solvents. The complexes showed strong absorption bands at around 560 (Q band) and 300 nm (B band) in chloroform, respectively. The complexes decomposed in solution under irradiation with visible light. The first oxidative or reductive half-wave potential of [B(OEt)(subpc)] was observed at 1.06 V (vs. SCE) or - 1.11 V, respectively.

Synthesis of Meso-Substituted Subphthalocyanine-Subporphyrin Hybrids: Boron Subtribenzodiazaporphyrins

The first syntheses of hybrid structures that lie between subphthalocyanines and subporphyrins are reported. The versatile single-step synthetic method uses a preformed aminoisoindolene to provide the bridging methine unit and its substituent while trialkoxyborates simultaneously act as Lewis acid, template, and provider of the apical substituent. The selection of each component therefore allows for the controlled formation of diverse, differentially functionalized systems. The new hybrids are isolated as robust, pure materials that display intense absorption and emission in the mid-visible region. The new compounds are further characterized in solution and solid state by variable-temperature NMR spectroscopy and X-ray crystallography, respectively.

Synthesis, Characterization, and Reactivity Studies of Subphthalocyanine Boron Triflate

The highly reactive subphthalocyanine boron triflate complex ((subPc)BOTf) was isolated and characterized by X-ray diffraction and spectroscopic methods. The combination of (subPc)BOTf and bis(trimethylsilyl)amide (LiHMDS) yielded a kinetically induced frustrated Lewis pair system capable of activating a variety of substrates such as ethers, amides, and ketones. These reactions demonstrate the high reactivity of (subPc)BOTf toward organic molecules.

Aluminum chloride activation of chloro-boronsubphthalocyanine: A rapid and flexible method for axial functionalization with an expanded set of nucleophiles

We have developed a process whereby chloro-boronsubphthalocyanine (Cl-BsubPc) and other BsubPcs are activated to reaction with oxygen, sulfur, and nitrogen based nucleophiles by treatment with aluminum chloride under mild conditions. This allows for the scope of atoms chemically bound to the boron atom to be expanded beyond those derived from the traditional oxygen and carbon based nucleophiles. The successful formation of thiophenoxy and phenylamino derivatives of BsubPc was confirmed spectroscopically and by X-ray crystallography of single crystals. We have proposed a detailed mechanism for this process based on experimental observation and NMR spectroscopy ( 1H, 11B, and 27Al) which involves formation of a complex between a halo-BsubPc and AlCl3 (which we denote BsubPc(Cl) ·Al(Cl′)3). Our observations indicate that the action of phenol on BsubPc(Cl) ·Al(Cl′)3 does not involve direct reaction at the boron atom; rather phenol first reacts at the aluminum atom along the way to the formation of a new intermediate complex BsubPc(OPh) ·Al(O′Ph)3. The consequence is that the rate of this process is independent of the nature of the starting BsubPc. Cl-BsubPc and Br-BsubPc as well as BsubPcs with peripheral substitutents all react to form their respective phenoxy derivatives at the same rate. Quenching of BsubPc(OPh) ·Al(O′Ph)3 with a Lewis base ultimately produces a new bond between the phenol nucleophile and the boron atom of the BsubPc.

Pseudohalides of boron subphthalocyanine

The synthesis and study of a series of pseudohalides of boron subphthalocyanine (BsubPc) are reported. Each pseudohalide has been compared to the more common chloride and bromide of BsubPc, and we have found that most react slower under standard phenoxyla

Observations regarding the crystal structures of non-halogenated phenoxyboronsubphthalocyanines having para substituents on the phenoxy group

We report the synthesis and systematic description of a series of five para-substituted phenoxy-BsubPcs including their characterization in the crystal state. The nature of the substituents on the phenoxy molecular fragment was chosen so as to vary both t

Triflate-subphthalocyanines: Versatile, reactive intermediates for axial functionalization at the boron atom

On the leave: Easily generated triflate boron subphthalocyanines are highly activated universal substrates for efficient axial substitution reactions with oxygen, sulfur, nitrogen, and carbon nucleophiles (see picture). Copyright

Chloro boron subphthalocyanine and its derivatives: Dyes, pigments or somewhere in between?

Nine derivatives of chloro boron subphthalocyanine (Cl-BsubPc, 1) have been synthesized and characterized. Seven dimers of Cl-BsubPc have been synthesized by reaction with biphenol (2a), bisphenol A (2b), bisphenol F (2c), bisphenol O (2d), bisphenol P (2

Effect of dual fullerenes on lifetimes of charge-separated states of subphthalocyanine - triphenylamine - fullerene molecular systems

Photoinduced intramolecular electron-transfer events of the newly synthesized subphthalocyanine-tripheny-lamine-fullerene triad (SubPc-TPA-Co 60) and subphthalocyanine-triphenylamine-bisfullerene tetrad (SubPc-TPA-(C60)2) were studied. The geometric and electronic structures of the triad were probed by ab initio B3LYP/3-21G method, which predicts SubPc-TPA.+-C60.- as a stable charge-separated state. The photoinduced events via the excited singlet state of SubPc were monitored by time-resolved emission measurements as well as transient absorption techniques. Efficient charge-separations via the excited states of SubPc were observed with the rates of a??1010 s _1. Compared with the SubPc - TPA dyad, a long-lived charge-separated state was observed for the SubPc - TPA - C60 triad with the lifetime of the radical ion pairs (??RIP) of 670 ns in benzonitrile. Interestingly, further charge stabilization was achieved in the charge-separated state of SubPc - TPA - (C60)2, in which the ??RIP was found to be 1050 ns in benzonitrile. ? 2008 American Chemical Society.