217. Phthalocyanines. Part VI. The structure of the phthalocyanines

Dent, C. E.; Linstead, R. P.; Lowe, AB

doi:10.1039/jr9340001033

Cited by 74 publications

(31 citation statements)

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“…[1][2][3] Since then, MPcs have been studied for use in chemical sensors, photodynamic therapy, optics, bioelectronics, molecular optoelectronic gates, and molecular neural networks. [4][5][6][7] Of particular importance is their application in organic semiconductors, discovered in 1948 by Eley.…”

Section: Introductionmentioning

confidence: 99%

Ground and excited states of zinc phthalocyanine, zinc tetrabenzoporphyrin, and azaporphyrin analogs using DFT and TDDFT with Franck-Condon analysis

Theisen

Huang

Fleetham

et al. 2015

The Journal of Chemical Physics

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Articles you may be interested inGround and excited states of zinc phthalocyanine, zinc tetrabenzoporphyrin, and azaporphyrin analogs using DFT and TDDFT with Franck-Condon analysis The electronic structure of eight zinc-centered porphyrin macrocyclic molecules are investigated using density functional theory for ground-state properties, time-dependent density functional theory (TDDFT) for excited states, and Franck-Condon (FC) analysis for further characterization of the UV-vis spectrum. Symmetry breaking was utilized to find the lowest energy of the excited states for many states in the spectra. To confirm the theoretical modeling, the spectroscopic result from zinc phthalocyanine (ZnPc) is used to compare to the TDDFT and FC result. After confirmation of the modeling, five more planar molecules are investigated: zinc tetrabenzoporphyrin (ZnTBP), zinc tetrabenzomonoazaporphyrin (ZnTBMAP), zinc tetrabenzocisdiazaporphyrin (ZnTBcisDAP), zinc tetrabenzotransdiazaporphyrin (ZnTBtransDAP), and zinc tetrabenzotriazaporphyrin (ZnTBTrAP). The two latter molecules are then compared to their phenylated sister molecules: zinc monophenyltetrabenzotriazaporphyrin (ZnMPTBTrAP) and zinc diphenyltetrabenzotransdiazaporphyrin (ZnDPTBtransDAP). The spectroscopic results from the synthesis of ZnMPTBTrAP and ZnDPTBtransDAP are then compared to their theoretical models and nonphenylated pairs. While the Franck-Condon results were not as illuminating for every B-band, the Q-band results were successful in all eight molecules, with a considerable amount of spectral analysis in the range of interest between 300 and 750 nm. The π-π * transitions are evident in the results for all of the Q bands, while satellite vibrations are also visible in the spectra. In particular, this investigation finds that, while ZnPc has a D 4h symmetry at ground state, a C 4v symmetry is predicted in the excited-state Q band region. The theoretical results for ZnPc found an excitation energy at the Q-band 0-0 transition of 1.88 eV in vacuum, which is in remarkable agreement with published gas-phase spectroscopy, as well as our own results of ZnPc in solution with Tetrahydrofuran that are provided in this paper. C 2015 AIP Publishing LLC. [http://dx

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Section: Introductionmentioning

confidence: 99%

Ground and excited states of zinc phthalocyanine, zinc tetrabenzoporphyrin, and azaporphyrin analogs using DFT and TDDFT with Franck-Condon analysis

Theisen

Huang

Fleetham

et al. 2015

The Journal of Chemical Physics

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“…[1][2][3][4][5][6][7] Initially after their discovery, phthalocyanines were predominantly used as pigments and dyes in the textile and paper industries because of their chemical, photochemical, and thermal stabilities. 8,9 In more recent decades the chemistry of substituted phthalocyanines has undergone tremendous growth, [10][11][12] and, in addition to traditional applications, substituted and unsubstituted phthalocyanines have found potential applications in industrial catalysis, [13][14][15][16][17][18] photosensitizers for photodynamic cancer therapy, 16,[19][20][21][22][23][24][25][26] markers for bioimaging, 27,28 antibacterial composites, [29][30][31][32] materials for ink-jet printing, 33 chemical sensors, [34][35][36][37] semiconductors, 38,39 functional polymers and liquid crystals, [40][41][42][43] light-harvesting modules for dye-sensitized solar cells and organic photovoltaics, …”

Section: Introductionmentioning

confidence: 99%

Synthetic approaches to asymmetric phthalocyanines and their analogues

Nemykin¹,

Dudkin²,

Dumoulin³

et al. 2014

Arkivoc

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This review summarizes synthetic strategies for the preparation of asymmetric phthalocyanines and their analogues. Cross-condensation between two phthalonitrile components, crosscondensation between one phthalonitrile and one non-nitrile component, targeted synthesis of AABB-type compounds, the subphthalocyanine ring-expansion method, as well as postmodification approaches on pre-formed symmetric and asymmetric systems, are discussed. Methodologies for targeted preparation of specific types of asymmetric phthalocyanines and their analogues are also briefly overviewed.

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“…The aza-nitrogen and peripheral fused benzene ring imparts chemical and thermal stability to the phthalocyanine macromolecule. The optical properties of metal phthalocyanine complexes have been studied extensively for several decades [1][2][3]. The low solubility of these complexes combined with the intense π−π* bands associated with phthalocyanine ligand led to the industrial applications as pigments in paints and dyestuffs [4].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Spectral, Magnetic, Thermal and Antimicrobial Studies on Symmetrically Substituted 2, 9, 16, 23-tetra- phenyliminophthalocyanine Complexes

Khan¹,

Reddy²,

Keshavayya³

2012

A Search for Antibacterial Agents

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217. Phthalocyanines. Part VI. The structure of the phthalocyanines

Abstract: Dent, Linstead, and Lowe : Phthalocyanines. Part V I . 1033 217, Phthalocyanines. Part V I . The Xtructure of the Phthalocyanines.

Cited by 74 publications

References 0 publications

Ground and excited states of zinc phthalocyanine, zinc tetrabenzoporphyrin, and azaporphyrin analogs using DFT and TDDFT with Franck-Condon analysis

Ground and excited states of zinc phthalocyanine, zinc tetrabenzoporphyrin, and azaporphyrin analogs using DFT and TDDFT with Franck-Condon analysis

Synthetic approaches to asymmetric phthalocyanines and their analogues

Synthesis, Spectral, Magnetic, Thermal and Antimicrobial Studies on Symmetrically Substituted 2, 9, 16, 23-tetra- phenyliminophthalocyanine Complexes

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