Generation of Triplet Excited States via Photoinduced Electron Transfer in meso-anthra-BODIPY: Fluorogenic Response toward Singlet Oxygen in Solution and in Vitro

被引：280

作者：

Filatov, Mikhail A. ^{[1
]}

Karuthedath, Safakath ^{[2
]}

Polestshuk, Pavel M. ^{[3
]}

Savoie, Huguette ^{[4
]}

Flanagan, Keith J. ^{[1
]}

Sy, Cindy ^{[1
]}

Sitte, Elisabeth ^{[1
]}

Telitchko, Maxime ^{[1
]}

Laquai, Frederic ^{[2
]}

Boyle, Ross W. ^{[4
]}

Senge, Mathias O. ^{[1
]}

机构：

[1] Univ Dublin, Trinity Coll Dublin, Trinity Biomed Sci Inst, Sch Chem,SFI Tetrapyrrole Lab, 152-160 Pearse St, Dublin 2, Ireland

[2] KAUST, KAUST Solar Ctr KSC, Phys Sci & Engn Div PSE, Mat Sci & Engn Program MSE, Thuwal 239556900, Saudi Arabia

[3] Moscow MV Lomonosov State Univ, Dept Chem, Leninskie Gory 1-3, Moscow 119991, Russia

[4] Univ Hull, Dept Chem, Cottingham Rd, Kingston Upon Hull HU6 7RX, Yorks, England

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2017年 / 139卷 / 18期

基金：

爱尔兰科学基金会;

关键词：

INTRAMOLECULAR CHARGE-TRANSFER; RADICAL-ION PAIRS; ENERGY; DONOR;

D O I：

10.1021/jacs.7b00551

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Heavy atom-free BODIPY-anthracene dyads (BADs) generate locally excited triplet states by way of photoinduced electron transfer (PeT), followed by recombination of the resulting charge-separated states (CSS). Subsequent quenching of the triplet states by molecular oxygen produces singlet oxygen (O-1(2)), which reacts with the anthracene moiety yielding highly fluorescent species. The steric demand of the alkyl substituents in the BODIPY subunit defines the site of O-1(2) addition. Novel bis- and tetraepoxides and bicyclic acetal products, arising from rearrangements of anthracene endoperoxides were isolated and characterized. O-1(2) generation by BADs in living cells enables visualization of the dyads distribution, promising new imaging applications.

引用

页码：6282 / 6285

页数：4

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