Iodo-BODIPY: a visible-light-driven, highly efficient and photostable metal-free organic photocatalyst

Li, Wenliang; Li, Leijiao; Xiao, Haihua; Qi, Ruogu; Huang, Yubin; Xie, Zhigang; Jing, Xiabin; Zhang, Hongxing

doi:10.1039/c3ra40932e

Cited by 108 publications

(93 citation statements)

References 48 publications

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“…BODIPY derivatives have recently emerged as one of the most prominent classes of organic dyes, with wide applications in fields such as fluorescent imaging and sensing, dye‐sensitized solar cells, lasing, non‐linear optics, photocatalysis, singlet oxygen generation and photodynamic therapy etc . These cis ‐constrained cyanines were first synthesized in 1968 (although the parent dye, 1 in Fig.…”

Section: Introductionmentioning

confidence: 99%

Fluorescence Quenching in BODIPY Dyes: The Role of Intramolecular Interactions and Charge Transfer

2017

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The fluorescence properties of the BODIPY dye and its two meso-substituted derivatives, tert-butyl-and phenyl-BODIPY, are rationalized. The non-emissive behavior of the latter two are attributed to the energetically accessible low-lying conical intersection between the ground state and the lowest excited singlet state. Both intramolecular non-covalent interactions and excited state charge transfer character are identified as being crucial for 'stabilizing' the intersection and prompting the nonradiative decay. Similar crossing was located in the bare BODIPY dye, however, being energetically less accessible, which correlates well with the high fluorescence quantum yields of the parent dye.

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Section: Introductionmentioning

confidence: 99%

Fluorescence Quenching in BODIPY Dyes: The Role of Intramolecular Interactions and Charge Transfer

2017

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“…Singlet quantum yield studies revealed that HBDP,M eBDP,a nd PhBDP have negligible ability to generate 1 O 2 .D ramatic increases of 0.81, 0.64, and 0.83 for HBDP-2I, MeBDP-2I, and PhBDP-2I, respectively,w ere observeda fter the incorporation of two iodine atoms into the BODIPYm otifs (Table 11). [73] These enhancements could be attributed to ar edistribution of the electron cloud caused by the presence of iodine atoms, which was verified by theoretical studies on the frontier molecular orbitalsb ased on ground-state structures.…”

Section: Carbon-sulfur Bond Cleavagementioning

confidence: 66%

Sulfur‐Center‐Involved Photocatalyzed Reactions

Wang

Jiang

2018

Chemistry An Asian Journal

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Sulfur-containing compounds (SCCs) exist widely in, for example, natural sources, pharmaceuticals, materials, and foods. Their multifarious functions have stimulated scientists to construct them in greener and more efficient ways and further exploit their properties. Different photosensitizers with sulfur atoms have been developed and exploited. Furthermore, SCCs display excellent ability in hydrogen-atom-transfer reactions. In addition to acting as catalysts, SCCs can also be efficiently transformed under visible-light-promoted conditions. Bond dissociation and oxygenation reactions that involve sulfur centers are emphasized here.

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“…However, it is difficult to stop the overoxidation of phenol with TiO 2 because the oxidation power of the hole produced by photoirradiation of TiO 2 is too strong to be controlled . In contrast to inorganic photocatalysts, metal‐free organic photocatalysts, the oxidation power of the excited state of which can be finely controlled, have been utilized as selective oxidation of substrates …”

Section: Photochemical Hydroxylation Of Benzene With Watermentioning

confidence: 99%

One‐Step Selective Hydroxylation of Benzene to Phenol

Fukuzumi

Ohkubo

2015

Asian J Org Chem

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Recent developments in the one-step thermal and photochemical catalytic hydroxylation of benzene to phenol using variouso xidants are described, focusingo nt he catalytic mechanisms. Hydroxylation of benzene with hydrogen peroxide is catalyzed by homogeneous metal complexes and heterogeneous metal oxides to produce phenol when high-valent metal-oxo complexes are reactive speciesT he selective hydroxylationo fb enzene to phenol is achieved by using mesoporous silica-alumina as the catalyst support, which prohibits further oxidation of phenol due to the strongly acidic sites. Photocatalytic oxidation of benzene with dioxygena nd water is made possible by using organic photocatalysts via photoinduced electron transfer from benzene to the excited states of the photocatalysts, followed by the hydroxylation of the benzene radicalc ation with water to yield phenols electively.T he further oxidation of phenol is prohibited because of the fast back electron transfer from the one-electron reduced species of the photocatalyst to the phenolr adical cation,w hereas back electron transfer from the one-electron reduceds pecies to the benzene radical cation is slowed down because of the large drivingf orce of the back electron transfer,w hichi si nt he Marcus inverted region. Catalytic Hydroxylationo fBenzene with H 2 O 2The selective hydroxylation of benzene derivatives with H 2 O 2 to phenol at ambient temperature was made possible by using [(tpa)Mn II ] 2 + (tpa = tris(2-pyridylmethyl)amine) incorporated in mesoporous silica-alumina (Al-MCM-41). [36] Nearly 100 %s electivity to phenol was achieved for the reaction system using [(tpa)Mn II ] 2 + @Al-MCM-41a nd benzene in an [a] S.

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Iodo-BODIPY: a visible-light-driven, highly efficient and photostable metal-free organic photocatalyst

Abstract: Iodo-BODIPY: a visible-light-driven, highly efficient and photostable metal-free organic photocatalyst3

Cited by 108 publications

References 48 publications

Fluorescence Quenching in BODIPY Dyes: The Role of Intramolecular Interactions and Charge Transfer

Fluorescence Quenching in BODIPY Dyes: The Role of Intramolecular Interactions and Charge Transfer

Sulfur‐Center‐Involved Photocatalyzed Reactions

One‐Step Selective Hydroxylation of Benzene to Phenol

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