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

被引：104
|
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
收藏
页码：392 / 395
页数：4
相关论文
共 50 条
  • [1] Functionalization of the 4,4-difluoro-4-bora-3a, 4a-diaza-s-indacene (BODIPY) core
    Li, Lingling
    Nguyen, Binh
    Burgess, Kevin
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (10) : 3112 - 3116
  • [2] Synthesis and properties of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY)-based conducting copolymers
    Cihaner, Atilla
    Algi, Fatih
    REACTIVE & FUNCTIONAL POLYMERS, 2009, 69 (01): : 62 - 67
  • [3] Synthesis of 3,5-diaryl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY®) dyes
    Thoresen, LH
    Kim, HJ
    Welch, MB
    Burghart, A
    Burgess, K
    SYNLETT, 1998, (11) : 1276 - +
  • [4] Synthesis of 8-heteroatom-substituted 4,4-difluoro-4-bora-3a, 4a-diaza-s-indacene dyes (BODIPY)
    Goud, Thirumani Venkateshwar
    Tutar, Ahmet
    Biellmann, Jean-Francois
    TETRAHEDRON, 2006, 62 (21) : 5084 - 5091
  • [5] Rapid and Selective Electrophilic Trifluoromethylation of the 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) Scaffold
    Santschi, Nico
    Cvengros, Jan
    Matthey, Coraline
    Otth, Elisabeth
    Togni, Antonio
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (29) : 6371 - 6375
  • [6] Synthesis of 8-substituted 4, 4-difluoro-4-bora-3a,4a-diaza-s-indacene Dyes (BODIPY)
    Tutar, Ahmet
    Erenler, Ramazan
    Biellmann, Jean-Francois
    JOURNAL OF THE CHEMICAL SOCIETY OF PAKISTAN, 2013, 35 (04): : 1197 - 1201
  • [7] 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene as a Bright Fluorescent Label for DNA
    Ehrenschwender, Thomas
    Wagenknechet, Hans-Achim
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (07): : 2301 - 2304
  • [8] A new conducting polymer bearing 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) subunit: Synthesis and characterization
    Cihaner, Atilla
    Algi, Fatih
    ELECTROCHIMICA ACTA, 2008, 54 (02) : 786 - 792
  • [9] Synthesis and characterization of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY)-labeled fluorescent ligands for the mu opioid receptor
    Emmerson, PJ
    Archer, S
    ElHamouly, W
    Mansour, A
    Akil, H
    Medzihradsky, F
    BIOCHEMICAL PHARMACOLOGY, 1997, 54 (12) : 1315 - 1322
  • [10] 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes modified for extended conjugation and restricted bond rotations
    Chen, J
    Burghart, A
    Derecskei-Kovacs, A
    Burgess, K
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10): : 2900 - 2906
12345