Synthesis and optical properties of push–pull type tetrapyrazinoporphyrazines

Lee, Bum Hoon; Jaung, Jae Yun; Jang, Se Chan; Yi, Sung Chul

doi:10.1016/j.dyepig.2004.06.022

Cited by 46 publications

(13 citation statements)

References 11 publications

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“…[12][13][14] Synthesised compounds 3a-d reacted with copper chloride in o-dichlorobenzene or 1-chloronaphthalene to form a tetramer. [15][16] An alternative method was used for compound 4b and the copper complex was not formed directly. Tetramerisation using magnesium turning and 1-butanol was performed first.…”

Section: Resultsmentioning

confidence: 99%

“…Anal. Calcd for C 120 H 112 MgN 16 Synthesis of metal-free tetraquinoxalinoporphyrazine; general procedure A mixture of Mg tetraquinoxalinoporphyrazine complex (0.6 g, 0.33 mmol) and p-toluenesulfonic acid (3.3 g, 16.5 mmol) in THF (5 mL) was stirred for 1 h at room temperature. After this, the solvent was removed under reduced pressure and the product crystallised with methanol then chromatographed on silica gel, using chloroform: MeOH = 30:1 as the eluent, to give the porphyrazine as a dark green solid, yield 51%, m.p.…”

Section: Synthesis Of Mg Complex; General Proceduresmentioning

confidence: 99%

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Synthesis and Spectral Characterisation of Dicyanopyrazine-related Cyanoheterocycles

Song

Jang

Wang

et al. 2013

Journal of Chemical Research

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Four dicyanopyrazine-related cyanoheterocycles have been synthesised and characterised; they show different absorption maxima values and molar absorptivity in absorption spectra. HOMO and LUMO energy levels have been obtained by electrochemical measurements and DMol3 calculation and show little difference in HOMO values but big differences in LUMO values. Their UV-Vis absorbance and fluorescence spectra have been investigated in chloroform and toluene and their aggregation decreases as the concentration decreases in toluene.

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Section: Resultsmentioning

confidence: 99%

Section: Synthesis Of Mg Complex; General Proceduresmentioning

confidence: 99%

Synthesis and Spectral Characterisation of Dicyanopyrazine-related Cyanoheterocycles

Song

Jang

Wang

et al. 2013

Journal of Chemical Research

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“…A c c e p t e d M a n u s c r i p Non-symmetrical octasubstituted TPyzPzs combining electron-donor 4-alkoxyphenyl and electron-acceptor 4-nitrophenyl-or 4-alkylsulfonylphenyl groups in each pyrazine ring (Chart 11) were prepared as Cu II complexes from the corresponding dinitriles Pyz40, Pyz41 and CuCl in o-DCB in the presence of ammonium molybdate with 25-35% yields [134] in order to study the optical properties of these push-pull type TPyzPzs.…”

Section: Page 14 Of 66mentioning

confidence: 99%

Tetrapyrazinoporphyrazines and their metal derivatives. Part I: Synthesis and basic structural information

Donzello

Ercolani

Novakova

et al. 2016

Coordination Chemistry Reviews

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“…Phthalocyanines (Pcs) also have different applications in the field of nonlinear optics [5][6][7], xerography [8], solar energy conversion [9], liquid crystalline charge carriers [10,11], catalysis [12], colorants [13,14] and photodynamic therapy (PDT) [15,16].…”

Section: Introductionmentioning

confidence: 99%

Structures and properties of metal-free and magnesium tetrathieno[2,3-b]porphyrazine investigated using density functional theory

Wang

Sun

et al. 2010

Sci. China Chem.

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Density functional theory (DFT) and time-dependent density functional theory (TD-DFT) calculation were adopted to study the structures and properties of metal-free and magnesium tetrathieno[2,3-b]porphyrazine (TTPPzH 2 and TTPPzMg) using B3LYP method with the 6-31G(d) basis set. A comparison of the geometrical structures, atomic charges, molecular orbitals, UV-vis spectra and infrared (IR) spectra among tetrathieno[2,3-b]porphyrazine (TTPPzH 2 ), phthalocyanine (H 2 Pc) and porphyrazine (H 2 Pz) compounds was performed. The substituent effect of the thiophene heterocycle for electron-donating on the structures and properties of these compounds has been discussed. Compared with other atoms, the charge distribution of C  atoms adjacent to the sulfur atom is significantly influenced by the thiophene heterocycle substituents. The enlargement of the HOMO-LUMO gaps from H 2 Pc and MgPc to TTPPzH 2 and TTPPzMg is at the origin of the observed blue shift of the Q band when moving from H 2 Pc to TTPPzH 2 compounds. Special emphasis has been devoted to the strongest B bands for TTPPzH 2 compounds which show red shift due to the large destabilization of the lower lying occupied orbitals compared with the corresponding B bands of H 2 Pc compounds. With the assistance of animated pictures produced on the basis of the normal coordinates, the significant peaks and vibration modes in the IR spectra of all the compounds were assigned and analyzed. tetrathieno[2,3-b]porphyrazine, DFT method, molecular structure, UV-vis spectra, IR spectra

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Synthesis and optical properties of push–pull type tetrapyrazinoporphyrazines

Cited by 46 publications

References 11 publications

Synthesis and Spectral Characterisation of Dicyanopyrazine-related Cyanoheterocycles

Synthesis and Spectral Characterisation of Dicyanopyrazine-related Cyanoheterocycles

Tetrapyrazinoporphyrazines and their metal derivatives. Part I: Synthesis and basic structural information

Structures and properties of metal-free and magnesium tetrathieno[2,3-b]porphyrazine investigated using density functional theory

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