Intramolecular Charge Transfer‐Enhanced BODIPY Photosensitizer in Photoinduced Electron Transfer and Its Application to Photoxidation under Mild Condition

Wang, Ruiqin; Geng, Ying; Zhang, Lili; Wu, Wenting; Fan, Weiyu; Li, Zhongtao; Wang, Lizhuo; Zhan, Liying; Wu, Xueyan; Wu, Mingbo

doi:10.1002/cjoc.201500494

Cited by 7 publications

(5 citation statements)

References 40 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…H 2 O 2 was detected by use of the KI/CH 3 COOH/starch system . A reddish-brown color was observed upon mixing the reaction system with KI/CH 3 COOH/starch in the presence of H 2 O 2 .…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Enhancing Selective Photooxidation through Co–Nx-doped Carbon Materials as Singlet Oxygen Photosensitizers

et al. 2017

Self Cite

View full text Add to dashboard Cite

Singlet oxygen ( 1 O 2 ) is considered one of the most effective and selective oxygen agents. However, it is always obtained with the help of heavy atoms in the photosensitizers to sensitize 3 O 2 . Herein, metal−nitrogen (M−Nx) doped 1 O 2 photosensitizers were readily prepared from metal−nitrogen complex. Their relative metal centers (e.g., Co) chelated with the N/C moiety (Co−Nx/C) provide the primary active sites for 1 O 2 generation and selective oxidation. The structures of Co−Nx active sites are investigated by scanning and transmission electron microscopy and X-ray photoelectron, Fourier transform infrared, and X-ray absorption fine structure spectroscopy. Their functions for 1 O 2 generation are confirmed by electrons spin resonance, 1 O 2 emission, KSCN poisoning test, and H 2 SO 4 etching test. These Co−Nx photosensitizers show excellent selective photooxidation abilities for 1,5-dihydroxynaphthalene after irradiation by a light-emitting diode lamp. After simple concentration and filtration, it is easy to obtain the pure product (juglone), which is confirmed by 1 H NMR spectroscopy. On the basis of density functional theory calculations, metal (e.g., Co) chelated with N/C moiety, especially for the Co−pyridinic N structure, could effectively reduce the singlet−triplet energy gap (ΔE ST ). It is speculated that this strategy for lowering ΔE ST could benefit intersystem crossing from the singlet state to the triplet state and efficient sensitization of 3 O 2 (triplet state) into 1 O 2 for selective photooxidation.

show abstract

“…H 2 O 2 was detected by use of the KI/CH 3 COOH/starch system . A reddish-brown color was observed upon mixing the reaction system with KI/CH 3 COOH/starch in the presence of H 2 O 2 .…”

Section: Resultsmentioning

confidence: 99%

“…A reddish-brown color was observed upon mixing the reaction system with KI/CH 3 COOH/starch in the presence of H 2 O 2 . Figure S6 shows that there is no H 2 O 2 present in the reaction system . Besides, 5,5-dimethyl-1-pyrroline- N -oxide (DMPO) was employed as scavenger for superoxide radical anion (O 2 – • ) in the system by ESR …”

Section: Resultsmentioning

confidence: 99%

Enhancing Selective Photooxidation through Co–Nx-doped Carbon Materials as Singlet Oxygen Photosensitizers

et al. 2017

Self Cite

View full text Add to dashboard Cite

show abstract

“…BODIPY photocatalysts have recently been used to oxidize 1,4-dihydropyridines [37]. A key characteristic of the BODIPY photocatalysts is the presence of methyl groups in the 1,7-positions of the BODIPY core to prevent rotation of the phenyl group in the 8-position, which reduces non-radiative decay of the excited state.…”

Section: Photoredox Chemistry With Bodipy Dyesmentioning

confidence: 99%

Redox Chemistry of BODIPY Dyes

Thompson¹,

Heiden²

2019

BODIPY Dyes - A Privilege Molecular Scaffold With Tunable Properties

View full text Add to dashboard Cite

The implementation of BODIPY dyes in electron transfer reactions is an exciting new frontier that expands the toolbox of the dye molecule that has primarily been implemented in biological and chemical sensing applications. BODIPY dyes are capable of reversible reductions at the average reduction potential of −1.53 V vs. ferrocene/ferrocenium, varying about 700 mV from this average value depending on the substitution of the BODIPY core. BODIPY dyes are also capable of reversible oxidations, exhibiting an average oxidation potential of 610 mV with the ability to manipulate the oxidation potential up to 600 mV from the average potential. The respective azaBODIPY dyes are on average about 600 mV easier to reduce (more positive potentials) and are oxidized at almost identical oxidation potentials to the respective BODIPY dyes. The oxidation and reduction potentials of BODIPY dyes are heavily dependent on substitution of the BODIPY core, which allows for a high degree of tunability in the redox potentials. This characteristic makes BODIPY dye molecules good candidates for use as photoredox catalysts, redox flow batteries, redox-active ligands, light harvesting antenna, and many other applications in materials science, biology, and chemical synthesis.

show abstract

“…These results suggest the existence of 1 O 2 ( Figure , c–d) . However, there are no obvious intensity changes, indicating that 1 O 2 is not involved into the first step of the catalytic cycle . In a separate experiment, the signal of O 2 ·‑ from the mixture of B2 and 1a was observed when DMPO was used as the radical scavenger under the same conditions.…”

Section: Resultsmentioning

confidence: 99%

“…However, there are no obvious intensity changes, indicating that 1 O 2 is not involved into the first step of the catalytic cycle. 30 In a separate experiment, the signal of O 2…”

Section: ■ Results and Discussionmentioning

confidence: 99%

BODIPY Photocatalyzed Beckmann Rearrangement and Hydrolysis of Oximes under Visible Light

et al. 2022

View full text Add to dashboard Cite

A novel, efficient, and mild protocol for rearrangement of oximes to amides or hydrolyzing to ketone/aldehyde using a simple BODIPY dye as a photocatalyst and air as an oxidant via propagation reaction under visible-light irradiation is reported. The triplet excited state of BODIPY played a significant role in the catalytic process. It was found that the various substituted ketoximes, both with electron-withdrawing and electron-donating substituents, afforded the corresponding products with moderate to excellent yields, and the catalytic efficiency was up to 0.01 mol %.

show abstract

Intramolecular Charge Transfer‐Enhanced BODIPY Photosensitizer in Photoinduced Electron Transfer and Its Application to Photoxidation under Mild Condition

Cited by 7 publications

References 40 publications

Enhancing Selective Photooxidation through Co–Nx-doped Carbon Materials as Singlet Oxygen Photosensitizers

Enhancing Selective Photooxidation through Co–Nx-doped Carbon Materials as Singlet Oxygen Photosensitizers

Redox Chemistry of BODIPY Dyes

BODIPY Photocatalyzed Beckmann Rearrangement and Hydrolysis of Oximes under Visible Light

Contact Info

Product

Resources

About