The synthesis and crystal structure of unsubstituted 4,4-difluoro-4-bora-3a, 4a-diaza-s-indacene (BODIPY)

被引：109

作者：

Tram, Kha ^{[1
]}

Yan, Hongbin ^{[1
]}

Jenkins, Hilary A. ^{[2
]}

Vassiliev, Serguei ^{[3
]}

Brucec, Doug ^{[3
]}

机构：

[1] Brock Univ, Dept Chem, St Catharines, ON L2S 3A1, Canada

[2] McMaster Univ, Dept Chem, Hamilton, ON L8S 4L9, Canada

[3] Brock Univ, Dept Biol, St Catharines, ON L2S 3A1, Canada

来源：

DYES AND PIGMENTS | 2009年 / 82卷 / 03期

基金：

加拿大自然科学与工程研究理事会;

关键词：

BODIPY; Fluorescence; Absorbance; Crystal structure; Dipyrromethane; DYES; PYRROMETHENES; COMPLEXES; BORON; DI;

D O I：

10.1016/j.dyepig.2009.03.001

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The fully unsubstituted 4,4-difluoro-4-bora-3a.4a-diaza-s-indacene (BODIPY) was synthesized for the first time by oxidation of dipyrromethane followed by treatment with boron trifluoride diethyl etherate in the presence of a base. The compound was fully characterized and its X-ray crystal structure is reported. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：392 / 395

页数：4

共 50 条

[31] Disabling Photoinduced Electron Transfer in 4,4-Difluoro-8(-4′-hydroxyphenyl)-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene by Phosphorylation [J].

Michaela Jacob ;

Alexander Schmitt ;

Gregor Jung .

Journal of Fluorescence, 2008, 18 :639-644

[32] Evidence For Transfer of Radicals between Oil-in-Water Emulsion Droplets as Detected by the Probe (E,E)-3,5-Bis(4-phenyl-1,3-butadienyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene, BODIPY665/676 [J].

Raudsepp, Piret ;

Bruggemann, Dagmar A. ;

Andersen, Mogens L. .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2014, 62 (51) :12428-12435

[33] Conversion of 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacenes (F-BODIPYs) to Dipyrrins with a Microwave-Promoted Deprotection Strategy [J].

Crawford, Sarah M. ;

Thompson, Alison .

ORGANIC LETTERS, 2010, 12 (07) :1424-1427

[34] First Highly Efficient and Photostable E and C Derivatives of 4,4-Difluoro-4-bora-3a, 4a-diaza- s- indacene ( BODIPY) as Dye Lasers in the Liquid Phase, Thin Films, and Solid- State Rods [J].

Duran-Sampedro, Gonzalo ;

Esnal, Ixone ;

Agarrabeitia, Antonia R. ;

Banuelos Prieto, Jorge ;

Cerdan, Luis ;

Garcia-Moreno, Inmaculada ;

Costela, Angel ;

Lopez-Arbeloa, Inigo ;

Ortiz, Maria J. .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (09) :2646-2653

[35] Synthesis of 3,5-dichloro-4,4-difluoro-4-bora-3a,4a-diaza-s-indacenes (BODIPYs) via Cu(OTf)2 mediated oxidative nucleophilic substitution of hydrogen by chloride [J].

Frank, Felicity ;

Alice, Laura Manzoli ;

Mauker, Philipp ;

Alsimaree, Abdulrahman A. ;

Waddell, Paul Gordon ;

Probert, Michael Richard ;

Penfold, Thomas James ;

Knight, Julian Gary ;

Hall, Michael John .

TETRAHEDRON, 2020, 76 (17)

[36] 8-(4-(3,4-Dicyano)phenoxyphenyl)-2,6-diethyl-4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene: Synthesis and photophysical properties [J].

Molchanov, Evgeniy E. ;

Gavrilova, Anna N. ;

Shushkova, Anastasia S. ;

Soshnikova, Vera A. ;

Ksenofontova, Ksenia, V ;

Maizlish, Vladimir E. ;

Dmitriev, Maxim, V ;

Abramov, Igor G. ;

Marfin, Yuriy S. .

OPTICAL MATERIALS, 2025, 159

[37] Synthesis and Optical Properties of p-(4,4-Difluoro-4-boron-3a,4a-diaza-s-indacene-8-yl)-4′-benzoyloxy-2-hydroxybenzaldehyde [J].

Gruzdev, M. S. ;

Chervonova, U. V. ;

Kolker, A. M. .

RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2016, 86 (08) :1973-1975

[38] Synthesis and optical properties of p-(4,4-difluoro-4-boron-3a,4a-diaza-s-indacene-8-yl)-4’-benzoyloxy-2-hydroxybenzaldehyde [J].

M. S. Gruzdev ;

U. V. Chervonova ;

A. M. Kolker .

Russian Journal of General Chemistry, 2016, 86 :1973-1975

[39] Photophysics of α-azinyl-substituted 4, 4-difluoro-8-(4-R-phenyl)-4-bora-3a, 4a-diaza-s-indacenes [J].

Pevtsov, Dmitry N. ;

Nikolenko, Lyubov M. ;

Nevidimov, Alexander V. ;

Tovstun, Sergey A. ;

Gadomska, Anna V. ;

Kuzmin, Vladimir A. ;

Razumov, Vladimir F. ;

Trestsova, Maria A. ;

Utepova, Irina A. ;

Chupakhin, Oleg N. ;

Shchepochkin, Alexander V. ;

Valeeva, Albina A. ;

Rempel, Andrey A. .

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2022, 432

[40] 8-[4-(2-Hydroxypropane-2-yl)phenyl]-1,3,4,4,5,7-hexamethyl-4-boron-3a,4a-diaza-S-indacene [J].

Zobnina, Anastasiya ;

Moskalensky, Alexander ;

Vorob'ev, Aleksey .

MOLBANK, 2021, 2021 (04)

← 1 2 3 4 5 →