Toward panchromatic organic functional molecules: Density functional theory study on the nature of the broad UV–Vis–NIR spectra of substituted tetra(azulene)porphyrins

Qi, Dongdong; Zhang, Lijuan; Jiang, Jianzhuang

doi:10.1016/j.jmgm.2012.06.001

Cited by 5 publications

(2 citation statements)

References 100 publications

(168 reference statements)

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“…As a result, the Q-band of 195.4 was intensified and shifted to longer wavelengths. The tetraazulene core present in 195.4 was subsequently investigated using DFT methods as a potential panchromatic organic chromophore …”

Section: Macrocyclic Systemsmentioning

confidence: 99%

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

et al. 2016

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Two-dimensionally extended, polycyclic heteroaromatic molecules (heterocyclic nanographenes) are a highly versatile class of organic materials, applicable as functional chromophores and organic semiconductors. In this Review, we discuss the rich chemistry of large heteroaromatics, focusing on their synthesis, electronic properties, and applications in materials science. This Review summarizes the historical development and current state of the art in this rapidly expanding field of research, which has become one of the key exploration areas of modern heterocyclic chemistry.

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Section: Macrocyclic Systemsmentioning

confidence: 99%

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

et al. 2016

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“…The reported tetra(anthracenyl)porphyrins (TAnPs) and tetra(azulene)porphyrins (TAzPs) have intense absorptions covering the broad UV, visible, and NIR range revealed in the electronic absorption spectrum. On the basis of analysis of electronic structures and electronic absorption spectra, Jiang et al found that the introduction of electron-withdrawing or electron-donating groups onto the periphery of the TAnP/TAzP skeleton can tune the gap between the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO), inducing an obvious shift of the absorption bands, and the introduction of electron-donating groups onto the periphery of anthracene at α positions and of azulene at ε positions (the positions are labeled in Figure ) lead to novel panchromatic dyes. , This indicates that fusing anthracene/azulene to porphyrin core is effective to extend absorption into NIR region.…”

Section: Introductionmentioning

confidence: 99%

Molecular Docking toward Panchromatic Dye Sensitizers for Solar Cells Based upon Tetraazulenylporphyrin and Tetraanthracenylporphyrin

Zhang¹,

Li²,

Yu-jie

et al. 2017

J. Phys. Chem. A

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Novel dye sensitizers are highly expected in the development of dye-sensitized solar cells (DSSCs) because dye sensitizers can significantly affect the power conversion efficiency (PCE). Here, the molecular docking strategy is applied to design panchromatic dye sensitizers for DSSCs to improve light-harvesting efficiency covering the full solar spectrum. Considering the broad absorption bands of tetraanthracenylporphyrins (TAnPs) and tetraazuleneporphyrins (TAzPs), based upon porphyrin dye sensitizer YD2-o-C8, the panchromatic dye sensitizers coded as H(TAnP)-α, H(TAzP)-γ, H(TAzP)-ε, and H(TAzP)-δ are designed by the substitution of the porphyrin-ring in YD2-o-C8 with TAnPs and TAzPs moieties at different positions. The geometries, electronic structures, and excitation properties of the designed dye sensitizers are investigated using density functional theory (DFT) and time-dependent DFT methods. The analysis of geometries, conjugation lengths, electronic structures, absorption spectra, transition configurations, exciton binding energies, and free energy variations for electron injection and dye regeneration supports that the designed molecules are effective to be applied as potential candidates of dye sensitizers for DSSCs. Among the designed dye sensitizers, H(TAzP)-γ and H(TAnP)-α must have the better performance in DSSCs.

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Spectroscopic and quantum chemical study of phthalocyanines with 1,4,7-trioxanonyl moieties

Wierzchowski

Sobotta

Łażewski

et al. 2020

Journal of Molecular Structure

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Toward panchromatic organic functional molecules: Density functional theory study on the nature of the broad UV–Vis–NIR spectra of substituted tetra(azulene)porphyrins

Cited by 5 publications

References 100 publications

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

Molecular Docking toward Panchromatic Dye Sensitizers for Solar Cells Based upon Tetraazulenylporphyrin and Tetraanthracenylporphyrin

Spectroscopic and quantum chemical study of phthalocyanines with 1,4,7-trioxanonyl moieties

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