Synthesis, Photophysical Properties and Two‐Photon Absorption Study of Tetraazachrysene‐based N‐Heteroacenes

Li, Gang; Wang, Shuai‐Hua; Yang, Shufan; Liu, Guangfeng; Hao, Pin; Zheng, Yusen; Long, Guankui; Li, Dandan; Zhang, Yu; Yang, Wenbin; Xu, Liang; Gao, Weibo; Zhang, Qichun; Cui, Guanwei; Tang, Bo

doi:10.1002/asia.201801656

Cited by 18 publications

(10 citation statements)

References 71 publications

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“…The compound was synthesized via a modification to the previously reported procedure . Compound 2 (9.0 g, 19.3 mmol) and sodium nitrite (0.44 g, 6.4 mmol) in acetic acid (91 mL) were cooled to 0 °C in an ice bath.…”

Section: Experimental Methodsmentioning

confidence: 99%

“…The compound was synthesized following the reported procedure . The product was obtained in quantitative yield as a dark purple solid.…”

Section: Experimental Methodsmentioning

confidence: 99%

“…This model system allows for the probing of synthetic accessibility of the dyes. Initially, the known literature route to the model dye was followed with the tosylation of 1 , nitration of 2 , deprotection of 3 , nitro reduction of 4 , NTz formation from 5 , , and double borylation of NTz through an Ir-catalyzed C–H activation to give the key coupling partner (Bpin) 2 NTz (Scheme ). After the significant screening of routes and conditions (Schemes S2 and S3; Table S6), a one-pot three-component Suzuki coupling of (Bpin) 2 NTz , 6 , and methyl-4-bromobenzoate awarded compound 7 ( TAA-NTz-Ph-COOMe ) in a 35% yield with a slight inseparable impurity in the 1 H NMR spectrum.…”

Section: Experimental Methodsmentioning

confidence: 99%

“…The compound was synthesized on a 10-g scale from naphthalenediamine (1) by following a reported procedure. 83 Pure compound 2 was obtained with a 77% yield as a solid as previously reported. This compound was carried forward as done previously in the literature.…”

Section: Prediction Of Open-circuit Voltage (V Oc )mentioning

confidence: 99%

“…The compound was synthesized via a modification to the previously reported procedure. 83 Compound 2 (9.0 g, 19.3 mmol) and sodium nitrite (0.44 g, 6.4 mmol) in acetic acid (91 mL) were cooled to 0 °C in an ice bath. Then, a solution of 70% HNO 3 (13.5 mL) in acetic acid (9 mL) was added dropwise, causing a temperature increase from 0 °C to 25 °C.…”

Section: Prediction Of Open-circuit Voltage (V Oc )mentioning

confidence: 99%

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Photophysical Properties of Donor–Acceptor−π Bridge–Acceptor Sensitizers with a Naphthobisthiadiazole Auxiliary Acceptor: Toward Longer-Wavelength Access in Dye-Sensitized Solar Cells

et al. 2022

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Accessing longer-wavelength photons is a critical research direction in dye-sensitized solar cells (DSSCs). Currently, dye-sensitized solar cells are exceptional at generating high photovoltages with shorter wavelength photons, but few examples exist of DSSCs using photons in the shortwave infrared region (>1000 nm). New dye building blocks are critical toward accessing these longer-wavelength photons. With this in mind, five new triphenylamine-based metal-free dyes derived from a donor−auxiliary acceptor−π bridge−acceptor (D−A′−π−A) structure are characterized theoretically for application in dye-sensitized solar cells (DSSCs). The driving force of electron injection, the spontaneity of dye regeneration, charge-transfer length, and partial density of states of the isolated and TiO 2 -bound dyes, which are all critical to DSSC performance, are systematically investigated via firstprinciples calculations. We find that replacing the high-performing benzothiadiazole (BTD) auxiliary acceptor building block with a longer conjugation length and stronger electron-withdrawing building block, naphtho[1,2-c:5,6-c′]bis([1,2,5]thiadiazole) (NTz), is beneficial toward the kinetics of charge injection along with reducing the optical energy gap of the designed dyes. The obtained results imply that using the NTz unit extends the absorption spectrum toward longer wavelengths and improves charge separation due to the planarity and conjugation length extension that arises from the NTz fragment. The shift of the conduction band of TiO 2 (ΔE CB value) is higher for the designed NTz-based dyes than for the BTD-based dye on TiO 2 , suggesting that the open-circuit voltage (V OC ) of a dye-sensitized solar cell device will also be higher. Concerning the photophysical properties of the dyes, the NTzbased dyes are promising as they possess a longer excited state and longer radiative lifetime than a BTD-based dye. We synthesize a model NTz-based dye and a BTD analogue for comparison with computational results. The optical properties of the NTz-based dye are computed to validate our computational approach, which agrees with the experimental observations. Our combined computational and experimental approach sheds light on the physical principle of molecular photogenerated charge transfer and provides valuable guidance for the further molecular synthesis of long-wavelength absorbing materials.

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Section: Experimental Methodsmentioning

confidence: 99%

“…The compound was synthesized following the reported procedure . The product was obtained in quantitative yield as a dark purple solid.…”

Section: Experimental Methodsmentioning

confidence: 99%

Section: Experimental Methodsmentioning

confidence: 99%

Section: Prediction Of Open-circuit Voltage (V Oc )mentioning

confidence: 99%

Section: Prediction Of Open-circuit Voltage (V Oc )mentioning

confidence: 99%

See 3 more Smart Citations

Photophysical Properties of Donor–Acceptor−π Bridge–Acceptor Sensitizers with a Naphthobisthiadiazole Auxiliary Acceptor: Toward Longer-Wavelength Access in Dye-Sensitized Solar Cells

et al. 2022

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Two‐Photon Absorption Enhancement by the Inclusion of a Tropone Ring in Distorted Nanographene Ribbons

et al. 2020

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An ew family of distorted ribbon-shaped nanographenes was designed, synthesized,a nd their optical and electrochemical properties were evaluated, pointing out an unprecedented correlation between their structural characteristics and the two-photon absorption (TPA) responses and electrochemical band gaps.Three nanographene ribbons have been prepared:aseven-membered-ring-containing nanographene presenting at ropone moiety at the edge,i ts full-carbon analogue,and apurely hexagonal one.W ehave found that the TPAc ross-sections and the electrochemical band gaps of the seven-membered-ring-containing compounds are higher and lower,respectively,than those of the fully hexagonal polycyclic aromatic hydrocarbon (PAH). Interestingly,t he inclusion of additional curvature has apositive effect in terms of non-linear optical properties of those ribbons.

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Two‐Photon Absorption Enhancement by the Inclusion of a Tropone Ring in Distorted Nanographene Ribbons

et al. 2020

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A new family of distorted ribbon‐shaped nanographenes was designed, synthesized, and their optical and electrochemical properties were evaluated, pointing out an unprecedented correlation between their structural characteristics and the two‐photon absorption (TPA) responses and electrochemical band gaps. Three nanographene ribbons have been prepared: a seven‐membered‐ring‐containing nanographene presenting a tropone moiety at the edge, its full‐carbon analogue, and a purely hexagonal one. We have found that the TPA cross‐sections and the electrochemical band gaps of the seven‐membered‐ring‐containing compounds are higher and lower, respectively, than those of the fully hexagonal polycyclic aromatic hydrocarbon (PAH). Interestingly, the inclusion of additional curvature has a positive effect in terms of non‐linear optical properties of those ribbons.

show abstract

Synthesis, Photophysical Properties and Two‐Photon Absorption Study of Tetraazachrysene‐based N‐Heteroacenes

Cited by 18 publications

References 71 publications

Photophysical Properties of Donor–Acceptor−π Bridge–Acceptor Sensitizers with a Naphthobisthiadiazole Auxiliary Acceptor: Toward Longer-Wavelength Access in Dye-Sensitized Solar Cells

Photophysical Properties of Donor–Acceptor−π Bridge–Acceptor Sensitizers with a Naphthobisthiadiazole Auxiliary Acceptor: Toward Longer-Wavelength Access in Dye-Sensitized Solar Cells

Two‐Photon Absorption Enhancement by the Inclusion of a Tropone Ring in Distorted Nanographene Ribbons

Two‐Photon Absorption Enhancement by the Inclusion of a Tropone Ring in Distorted Nanographene Ribbons

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