FormyIBODIPYs by PCC-Promoted Selective Oxidation of α-MethylBODIPYs. Synthetic Versatility and Applications

被引：17

作者：

Ramos-Torres, Agata ^{[1
]}

Avellanal-Zaballa, Edurne ^{[2
]}

Prieto-Castaneda, Alejandro ^{[1
]}

Garcia-Garrido, Fernando ^{[1
]}

Banuelos, Jorge ^{[2
]}

Agarrabeitia, Antonia R. ^{[1
]}

Ortiz, Maria J. ^{[1
]}

机构：

[1] Univ Complutense Madrid, Fac Ciencias Quim, Dept Quim Organ, Ciudad Univ S-N, E-28040 Madrid, Spain

[2] Univ Pais Vasco EHU, Dept Quim Fis, Apartado 644, Bilbao 48080, Spain

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 12期

关键词：

FLUORESCENT BODIPY DYES; PHOTOSENSITIZERS; COMPLEXES; CYANIDE; PROBES;

D O I：

10.1021/acs.orglett.9b01465

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthesis of formylBODIPYs has been established based on an oxidation with PCC of 3-methylBODIPYs. It has been demonstrated that this reagent can oxidize methyl groups at such position of the BODIPY core, regardless of its substitution pattern. Moreover, through this procedure it is possible to synthesize 8-aryl-3,5-diformylBODIPYs, which are otherwise difficult to obtain. These precursors have been functionalized to develop fluorescent sensors of amino acids or photosensitizers for singlet oxygen generation.

引用

页码：4563 / 4566

页数：4

共 30 条

[1] BODIPY Dye, the Most Versatile Fluorophore Ever? [J].

Banuelos, Jorge .

CHEMICAL RECORD, 2016, 16 (01) :335-348

[2] π-Extended tetrathiafulvalene BODIPY (ex-TTF-BODIPY): a redox switched "on-off-on'' electrochromic system with two near-infrared fluorescent outputs [J].

Bill, Nathan L. ;

Lim, Jong Min ;

Davis, Christina M. ;

Bahring, Steffen ;

Jeppesen, Jan O. ;

Kim, Dongho ;

Sessler, Jonathan L. .

CHEMICAL COMMUNICATIONS, 2014, 50 (51) :6758-6761

[3] Postfunctionalization of the BODIPY Core: Synthesis and Spectroscopy [J].

Boens, Noel ;

Verbelen, Bram ;

Dehaen, Wim .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (30) :6577-6595

[4] Fluorescent indicators based on BODIPY [J].

Boens, Noel ;

Leen, Volker ;

Dehaen, Wim .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (03) :1130-1172

[5] PYRROMETHENE-BF2 COMPLEXES AS LASER-DYES .2. [J].

BOYER, JH ;

HAAG, AM ;

SATHYAMOORTHI, G ;

SOONG, ML ;

THANGARAJ, K ;

PAVLOPOULOS, TG .

HETEROATOM CHEMISTRY, 1993, 4 (01) :39-49

[6] Fluorescent and colorimetric probes for detection of thiols [J].

Chen, Xiaoqiang ;

Zhou, Ying ;

Peng, Xiaojun ;

Yoon, Juyoung .

CHEMICAL SOCIETY REVIEWS, 2010, 39 (06) :2120-2135

[7] Boron Asymmetry in a BODIPY Derivative [J].

Haefele, Alexandre ;

Zedde, Chantal ;

Retailleau, Pascal ;

Ulrich, Gilles ;

Ziessel, Raymond .

ORGANIC LETTERS, 2010, 12 (08) :1672-1675

[8] β-Formyl-BODIPYs from the Vilsmeier-Haack Reaction [J].

Jiao, Lijuan ;

Yu, Changjiang ;

Li, Jilong ;

Wang, Zhaoyun ;

Wu, Min ;

Hao, Erhong .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (19) :7525-7528

[9] BODIPY dyes in photodynamic therapy [J].

Kamkaew, Anyanee ;

Lim, Siang Hui ;

Lee, Hong Boon ;

Kiew, Lik Voon ;

Chung, Lip Yong ;

Burgess, Kevin .

CHEMICAL SOCIETY REVIEWS, 2013, 42 (01) :77-88

[10] A novel near-infrared ratiometric fluorescent probe for cyanide and its bioimaging applications [J].

Kang, Jin ;

Huo, Fangjun ;

Zhang, Yongbin ;

Chao, Jianbin ;

Glass, Timothy E. ;

Yin, Caixia .

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2019, 209 :95-99

← 1 2 3 →