Subphthalocyanine azaanalogues – Boron(III) subporphyrazines with fused pyrazine fragments

Stuzhin, Pavel A.; Skvortsov, I. A.; Zhabanov, Yuriy A.; Сомов, Н. В.; Razgonyaev, O. V.; Nikitin, Ivan A.; Койфман, О. И.

doi:10.1016/j.dyepig.2018.11.006

Cited by 32 publications

(28 citation statements)

References 43 publications

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“…[19,20,21] Similar cyclotrimerization with formation of subporphyrazine macrocycle was also observed for heterocyclic vicinal dinitriles (e.g. with pyrazine [22] or 1,2,5-chalcogenadiazole rings [11b,23] ) and for alkyl and alkylsulfanyl substituted maleodinitriles. [24,25] It was reported that alkyl or aryl substituted fumarodinitriles having trans-configuration are inactive in cyclotrimerization with formation of subporphyrazines.…”

Section: Synthesismentioning

confidence: 67%

“…For B III complex of non-fluorinated hexaphenylsubporphyrazine and other aryl substituted subporphyrazines the very low fluorescence was also observed (Ф F < 0.001-0.03 [14] ). At the same time boron(III) complexes of more rigid 1,2,5-thiadiazole and pyrazine fused subporphyrazines exhibit stronger fluorescence (Ф F = 0.11-0.15 [23] ), and phenyl substitution on pyrazine rings even increases it (Ф F = 0.31 [22] ). Therefore we can make a general conclusion that aryl substituted porphyrazines and subporphyrazines are more sensitive to the factors causing deformation of the macrocycle and promoting radiationless deactivation of the excited states than more rigid (sub)porphyrazines with fused heteroarenes.…”

Section: Perfluorinated (Sub)porphyrazinesmentioning

confidence: 99%

“…Fluorescence was measured on Shimadzu RF-6000 spectrofluorophotometer. Fluorescence quantum yields were determined by comparative method using ZnPc as a refer-ence (Ф F = 0.32 in THF) as described in [22] . Commercially available solvents were dried and distilled prior use.…”

Section: Generalmentioning

confidence: 99%

“…In the spectra of non-fluorinated phenyl substituted macrocyclic complexes the intense charge transfer (CT) band from peripheral aryl groups to the central macrocycle is observed: Ar→subporphyrazine at ca. 400 nm [14,22] or Ph→porphyrazine at 450-480 nm [5,6] ). This CT band disappears when peripheral phenyl groups are perfluorinated and become strong electron-acceptors.…”

Section: X-ray Crystal Structure Of Trans-1mentioning

confidence: 99%

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Perfluorinated Porphyrazines. 5. Perfluoro-a,b-dicyanostylbene: Molecular Structure and Derived (Sub)Porphyrazine Complexes with IIIa Group Elements

Ivanova¹,

Лебедева²,

Сомов³

et al. 2019

MHC

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Template cyclomerization of perfluoro-a,b-dicyanostylbene in the presence of trichlorides of IIIa group elements results in formation of pentafluorophenyl substituted boron(III) subpophyrazinate ([(Cl)BsPAF 30 ]) and aluminum(III) and gallium(III) porphyrazinates ([(Cl)MPAF 40 ], M=Al, Ga). Their spectral-luminescence properties are discussed, revealing blue shift of the Q-band and brighter fluorescence comparatively to non-fluorinated analogues. In addition, the molecular structure of trans-perfluoro-a,b-dicyanostylbene was determined by single crystal X-ray diffraction.

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Section: Synthesismentioning

confidence: 67%

Section: Perfluorinated (Sub)porphyrazinesmentioning

confidence: 99%

Section: Generalmentioning

confidence: 99%

Section: X-ray Crystal Structure Of Trans-1mentioning

confidence: 99%

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Perfluorinated Porphyrazines. 5. Perfluoro-a,b-dicyanostylbene: Molecular Structure and Derived (Sub)Porphyrazine Complexes with IIIa Group Elements

Ivanova¹,

Лебедева²,

Сомов³

et al. 2019

MHC

Self Cite

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“…The electron-accepting properties of the Cl 6 SubPc molecule can be further enhanced by substituting the carbon atoms not bonded to chlorine with the more electronegative nitrogen. Such subporphyrazine-type compounds are synthesized in our group [24,68]. However, the deep-lying HOMOs often cause a decrease in the specific conductivity of the bulk material.…”

Section: Current Status and Perspectivesmentioning

confidence: 99%

Hexachlorinated Boron(III) Subphthalocyanine as Acceptor for Organic Photovoltaics: A Brief Overview

Pakhomov¹,

Travkin²,

Stuzhin³

2020

Recent Advances in Boron-Containing Materials

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A boron(III) complex of peripherally hexachlorinated subphthalocyanine, Cl 6 SubPc is a very promising small-molecule acceptor for application in organic photovoltaics. In this chapter the recent experimental results in the field are compared, and a critical review is given of the published works on the solar cells with the planar or bulk heterojunction architectures. The thin film properties of Cl 6 SubPc are also considered. The approaches to the further modification of the molecular structure of boron(III) subphthalocyanine-type compounds for the enhancement of their photoelectrical properties are discussed.

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Electronic Structure, Bonding, and Stability of Boron Subphthalocyanine Halides and Pseudohalides

Hildebrand

Holst

Bender

et al. 2022

Advcd Theory and Sims

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Halides and pseudohalides of boron subphthalocyanine (BsubPc) are promising candidates for efficient yet stable organic photovoltaics. Here, the electronic structure of such molecules, obtained using density functional theory, is considered. Based on the calculations, it is found that the tetrameric boron bond is stabilized by an inductive effect at the axial substituent and by conjugative effects across the ring system. It is further found that stability is dictated mostly by the axial moiety, such that Br-BsubPc is the most fitting precursor structure for further synthesis steps, whereas F-BsubPc is the most suitable candidate for long-term device performance. H-BsubPc is examined as a new BsubPc derivative, and found to be too volatile for long term device performance. Finally, it is shown that peripheral substitution dictates the position of frontier orbitals, thereby allowing for essentially separate optimization of material properties and material stability.

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Subphthalocyanine azaanalogues – Boron(III) subporphyrazines with fused pyrazine fragments

Cited by 32 publications

References 43 publications

Perfluorinated Porphyrazines. 5. Perfluoro-a,b-dicyanostylbene: Molecular Structure and Derived (Sub)Porphyrazine Complexes with IIIa Group Elements

Perfluorinated Porphyrazines. 5. Perfluoro-a,b-dicyanostylbene: Molecular Structure and Derived (Sub)Porphyrazine Complexes with IIIa Group Elements

Hexachlorinated Boron(III) Subphthalocyanine as Acceptor for Organic Photovoltaics: A Brief Overview

Electronic Structure, Bonding, and Stability of Boron Subphthalocyanine Halides and Pseudohalides

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