Synthesis and optical properties of axially bromo-substituted subphthalocyanines

Cao, Weifeng; Tu, Haiyang; Wang, Jing; Tian, He; Wang, Yang; Gu, Donghong; Gan, Fuxi

doi:10.1016/s0143-7208(02)00038-4

Cited by 14 publications

(17 citation statements)

References 14 publications

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“…350 nm . In analogy with porphyrins, the spectroscopic features of subporphyrinoids have been already applied in several fields, i.e., photodynamic therapy, organic photovoltaic cells, , optical information recording media, , and organic light-emitting diodes. , …”

Section: Introductionmentioning

confidence: 99%

“…350 nm. 32 In analogy with porphyrins, the spectroscopic features of subporphyrinoids have been already applied in several fields, i.e., photodynamic therapy, 33 organic photovoltaic cells, 34,35 optical information recording media, 36,37 and organic light-emitting diodes. 34,38 Unsurprisingly, these subporphyrinoid structures have been studied theoretically, notably using density functional theory (DFT) and its time-dependent extension (TD-DFT).…”

Section: ■ Introductionmentioning

confidence: 99%

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Structural and Optical Properties of Subporphyrinoids: A TD-DFT Study

2017

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Using ab initio approaches accounting for environmental effects, we investigate the ground- and excited-state properties of four subporphyrinoids: subporphyrin, subporphyrazine, tribenzosubporphyrin, and subphthalocyanine. We first show that the selected level of theory, that is DFT(PBE0), is able to reproduce the structure and NMR spectra of all compounds. The aromaticity of these four macrocyclic entities are next quantified and it is showed that these bowl-shape induced molecules present very strong aromatic characters. Next we analyze the spectral signatures of all four compounds using an approach going beyond the vertical approximation. The 0-0 energies are reproduced with a mean absolute deviation smaller than 0.1 eV, and the very good agreement obtained between experimental and theoretical band shapes allows us to unravel the vibronic contributions responsible to the specific band shapes of these subporphyrinoids. Finally, we investigate a large series of substituted subporphyrins, demonstrate the quality of the trends that are obtained with theory and design new compounds presenting red-shifted optical bands.

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Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Structural and Optical Properties of Subporphyrinoids: A TD-DFT Study

2017

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“…2 For this reason BsubPc is often referenced as the anomalous phthalocyanine in texts and review articles. 3 Its non-planar yet conjugated structure exhibits unique optoelectronic properties which have been investigated by researchers for application in devices such as organic light emitting diodes (OLEDs), 4 organic solar cells, 5 optical storage (such as DVDs), 6 and field effect transistors. 7 It has also been studied as a building block for molecular cages.…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2010

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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 (2e), bisphenol S (2f) and bisphenol Z (2g). For comparison two monomeric phenoxy- (3a) and 4-methylphenoxy (3b) BsubPcs have also been synthesized. Crystals were grown for dimer 2c, whereas all attempts to grow crystals of the remaining dimers resulted in the formation of molecular glasses or amorphous precipitates. Analysis on the structure of 2c suggests that the rigidity and aromatic nature of the central bisphenolic directs the crystal packing. The solubility of the BsubPc dimers in a variety of common organic solvents was measured and compared to that of Cl-BsubPc (2) and monomers 3a and 3b. We have defined ranges for classifying BsubPc derivatives based on their solubility in these solvents: pigment < or = 1 x 10(-8) M, 1 x 10(-3) M < or = pigment-like > 1 x 10(-8) M, 1 x 10(-2) M < or = dye-like > 1 x 10(-3) M, and dye > 1 x 10(-2) M. From this Cl-BsubPc (1) and compounds 2a, 2b, 2c, 2e and 2g are pigment-like while compounds 2d, 2f, 3a and 3b are dye-like. None are exclusively pigments or dyes. In this first approximation of this dye versus pigment classification we have not considered other processes besides solvation which could be undesirable such as polymorphic changes or Ostwald ripening. We have concluded that derivatization of Cl-BsubPc (1) with bisphenols and phenols can be used to control the solubility of BsubPc derivatives. We have also concluded that Cl-BsubPc (1) should not be considered a dye rather is pigment-like in its solubility.

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“…Phthalocyanines (Pcs) and their derivatives are excellent organic semiconductors and they have potential applications in field effect transistors, 1,2 xerography, 3 photoswitches, 4 laser recording materials, 5 photovoltaic cells, 6,7 and electrochemical sensors. 8,9 Among them, the electrochemistry usages of metallophthalocyanines (MPcs) have been the focus of numerous investigations from their superior electron transfer capacities, 10 which are due to the interaction between the phthalocyanine ring and the metal center.…”

Section: Introductionmentioning

confidence: 99%