Synthesis and Properties of Extracomplexes of Tetrasubstitued Phthalocyanines

Shaposhnikov, G. P.; Майзлиш, В. Е.; Kulinich, V. P.

doi:10.1007/s11176-005-0519-0

Cited by 8 publications

(4 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…These results suggest that the effect of an SF 5 ‐substitution at a peripheral α‐position is much larger than that at a β‐position. The blue‐shift caused by α‐substitution arises due to the presence of an electron‐withdrawing NO 2 group, which is the opposite observation to that seen when an electron‐donating n ‐butoxy ( n BuO) group is present; in that case, α‐substitution induces a red‐shift of the Q‐band …”

Section: Figurementioning

confidence: 88%

“…These results suggest that the effect of an SF 5 -substitution at ap eripheral a-position is much larger than that at a b-position. The blue-shiftc aused by a-substitutiona rises due to the presence of an electron-withdrawingN O 2 group, [16] which is the opposite observation to that seen when an electron-donating n-butoxy( nBuO) group is present;i nt hat case, a-substitution induces ared-shift of the Q-band. [17] To considert he origin of the differences in Q-bands, HOMO-LUMO energy levels of 3a-c were next calculated by computation, and they were comparedw ith those of conventionalz inc phthalocyanine (ZnPc) (DFT/B3LYP/6-31G*) (Figure 3).…”

mentioning

confidence: 97%

See 1 more Smart Citation

Synthesis of Phthalocyanines with a Pentafluorosulfanyl Substituent at Peripheral Positions

et al. 2015

View full text Add to dashboard Cite

The pentafluorosulfanyl (SF5) group is more electronegative, lipophilic and sterically bulky relative to the well‐explored trifluoromethyl (CF3) group. As such, the SF5 group could offer access to pharmaceuticals, agrochemicals and optoelectronic materials with novel properties. Here, the first synthesis of phthalocyanines (Pcs), a class of compounds used as dyes and with potential as photodynamic therapeutics, with a SF5 group directly attached on their peripheral positions is disclosed. The key for this work is the preparation of a series of SF5‐containing phthalonitriles, which was beautifully regio‐controlled by a stepwise cyanation via ortho‐lithiation/iodination from commercially available pentafluorosulfanyl arenes. The macrocyclization of the SF5‐containing phthalonitriles to SF5‐substituted Pcs required harsh conditions with the exception of the synthesis of β‐SF5‐substituted Pc. The regiospecificity of the newly developed SF5‐substituted Pcs observed by UV/Vis spectra and fluorescence quantum yields depend on the peripheral positon of the SF5 group.

show abstract

Section: Figurementioning

confidence: 88%

mentioning

confidence: 97%

Synthesis of Phthalocyanines with a Pentafluorosulfanyl Substituent at Peripheral Positions

et al. 2015

View full text Add to dashboard Cite

show abstract

“…This mixture was kept at 150 C for 48 h. After washing with acetone and separation by centrifugation, the resulting material (designated KaPCNO 2 ) was characterized. Data were compared with the results obtained for aluminum (III) tetranitrometallophthalocyanine (Al(III)TNMPc) obtained by conventional route using solvent and conventional aluminium source from metallic salt according Shaposhnikov [18], that consisting in react one organic ligand that containing nitro groups (4-nitrophthalonitrile) in contact with metallic specie at temperature near to 210e220 C. Fig. 1 shows a schematic representation of the new synthetic route used to prepare and immobilize metallophthalocyanine on kaolinite.…”

Section: Synthesis and Immobilization Of Metallophthalocyanine On Kaomentioning

confidence: 99%

New strategies for synthesis and immobilization of methalophtalocyanines onto kaolinite: Preparation, characterization and chemical stability evaluation

et al. 2016

View full text Add to dashboard Cite

This study presents results concerning the one-step synthesis and immobilization of a metallophthalocyanine on kaolinite as support/catalyst. X-ray diffractometry (XRD), nuclear magnetic resonance (NMR) and infrared (FTIR), UV/Visible (UV/Vis) and X-ray photoelectron (XPS) spectroscopies, thermal analyses, textural analyses (BET) and scanning electron microscopy (SEM) aided for the characterization of the materials. The FTIR, XPS and UV/Vis absorption spectra confirmed metallophthalocyanine formation. XRD analysis provided data on the structural disorganization of kaolinite during the synthesis of metallophthalocyanine, corroborated by SEM. NMR revealed that partial dissolution of aluminum from the octahedral kaolinite sheets was possible, which should release Al into the medium and, together with phthalonitrile, promote cyclomerization of the phthalocyanine macrocycle.

show abstract

“…В органической химии, из всего многообразия органических веществ, для нас большой интерес представляют высокомолекулярные соединения, которые имеют циклическое строение и содержат не менее двенадцати атомов в большом внутреннем цикле (атомов азота, углерода, серы, металла), так называемые макрогетероциклические соединения различной структурной модификации [1][2][3]. Структурные изменения данных соединений являются перспективными для получения веществ с ценными практическими свойствами.…”

unclassified

BGR Macroheterocyclic Compounds of Asymmetric Structure With Thiadiazol Fragments. Synthesis and Properties

Berezina¹,

Medvedeva²

2020

IVKKT

View full text Add to dashboard Cite

This communication is a continuation of the systematic research of the authors in the field of synthesis and study of the properties of macroheterocyclic compounds. The great potential for structural modification allows us to synthesize macroheterocyclic compounds that differ in composition and the nature of the heteroatoms that make up them and make this class of compounds promising from the point of view of the design for the preparation of substances with valuable practical properties. The interaction of N,N/-bis-(1-imino-2-phenyl-1H-indene-3-iliden)-1,4-phenylenediamine with 2,5-dimiano-1,3,4-thiadiazole and 3,5-diamino-1,2,4-thiadiazole the macroheterocyclic compounds of asymmetric structure were synthesized in the molar ratio of the initial substances. Macroheterocycles are powdered substances with different shades of red color, having melting and crystallization temperatures (investigated in the argon current), soluble in chloroform, DMF, acetone, ethanol. Purification was carried out by column chromatography on aluminum oxide of II degree of activity on Brockman (eluent acetone - chloroform, 1:9 by volume). Identification of synthesis products was performed by thin-layer chromatography on Silufol UV-254 plates (eluent – acetone - chloroform, 1:1 by volume). The obtained compounds were characterized by infrared and electron spectroscopy. The electronic absorption spectra were measured on a Hitachi U-2010 instrument in quartz cuvettes at 20 °C. IR spectra were obtained on the Avatar 360 FT-IR ESP device in KVG. Elemental analysis data were obtained using the CHNS-O Analyzer FlashEA of 1112 Series. A bathochromic shift of the absorption bands was noted when the compound with 1,3,4-thiadiazole was closed in a cycle. The spectral characteristics indicate that the molecules of the synthesized compounds do not have a flat structure and the absorption is due to individual fragments that are part of the molecules of the synthesized structures.

show abstract

Synthesis and Properties of Extracomplexes of Tetrasubstitued Phthalocyanines

Abstract: Extracomplexes of metals of groups III and IV of the periodic system with tetrasubstitued phthalocyanines containing halogen atoms, nitro-, amino-, hydroxy-, cyano-, and tert-butyl groups as substituents were synthesized. Their spectral and other properties were characterized.

Cited by 8 publications

References 6 publications

Synthesis of Phthalocyanines with a Pentafluorosulfanyl Substituent at Peripheral Positions

Synthesis of Phthalocyanines with a Pentafluorosulfanyl Substituent at Peripheral Positions

New strategies for synthesis and immobilization of methalophtalocyanines onto kaolinite: Preparation, characterization and chemical stability evaluation

BGR Macroheterocyclic Compounds of Asymmetric Structure With Thiadiazol Fragments. Synthesis and Properties

Contact Info

Product

Resources

About