| 词条 | BODIPY |
| 释义 |
PropertiesBODIPY dyes have been well investigated. Most BODIPY dyes have small Stokes shift and are relatively chemically inert. Fluorescence is quenched in a solution, which limits application. This problem has been handled by synthesizing asymmetric boron complexes and replacing the fluorine groups with phenyl groups. BODIPY dyes are notable for their uniquely small Stokes shift, high, environment-independent fluorescence quantum yields, often approaching 100% even in water, sharp excitation and emission peaks contributing to overall brightness, and high solubility in many organic solvents. The combination of these qualities makes BODIPY fluorophores promising for imaging applications. The position of the absorption and emission bands remain almost unchanged in solvents of different polarity as the dipole moment and transition dipole are mutually orthogonal. SynthesisBODIPY are prepared by treating a dipyrromethene precursor with boron trifluoride etherate in the presence of a tertiary amine.[6] Dipyrromethenes are accessed from a suitable pyrrole by several methods. Normally, one alpha-position in employed pyrroles is substituted and the other is free. Condensation of such pyrrole, often available from Knorr pyrrole synthesis, with an aromatic aldehyde in the presence of TFA gives dipyrromethane, which is oxidized to dipyrromethene using a quinone oxidant such as DDQ or p-chloranil. Alternatively, dipyrromethenes are prepared by treating a pyrrole with an activated carboxylic acid derivative, usually an acyl chloride. Unsymmetrical dipyrromethenes can be obtained by condensing pyrroles with 2-acylpyrroles. Intermediate dipyrromethanes may be isolated and purified, but isolation of dipyrromethenes is usually compromised by their instability. {{clear left}} Structures and reactivityThe BODIPY core has a rich chemistry and variety of substitutions due to the high tolerance for pyrrole and aldehyde (or acyl chloride) starting materials.[6] The core carries a formal negative charge on the boron atom, and a formal positive charge on one of the nitrogen atoms. The boron atom can also be post-functionalised to exchange the fluorine atoms for strong nucleophilic reagents, such as lithiated alkyne or aryl species.[6] Hydrogen atoms at the 2 and 6 positions of the cyclic core can be displaced by halogen atoms using succinimide reagents such as NCS, NBS and NIS - which allows for further post-functionalisation through palladium coupling reactions with boronate esters, tin reagents etc.[6] Potential applicationsBODIPY conjugates are widely studies as potential sensors and for labelling. Oligonucleotides have been labelled for sequencing for example.[7] References1. ^Alfred Treibs und Franz-Heinrich Kreuzer. Difluorboryl-Komplexe von Di- und Tripyrrylmethenen. Justus Liebigs Annalen der Chemie 1968, 718 (1): 208-223.}} 2. ^{{cite journal | title = Synthesis of the Core Compound of the BODIPY Dye Class: 4,4′-Difluoro-4-bora-(3a,4a)-diaza-s-indacene |author1=A. Schmitt |author2=B. Hinkeldey |author3=M. Wild |author4=G. Jung | doi = 10.1007/s10895-008-0446-7 |pmid=19067126 | journal = J. Fluoresc. | year = 2009 | volume = 19 | pages = 755–759 | issue = 4}} 3. ^{{cite journal | title = The synthesis and crystal structure of unsubstituted 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) |author1=K. Tram |author2=H. Yan |author3=H. A. Jenkins |author4=S. Vassiliev |author5=D. Bruce | doi = 10.1016/j.dyepig.2009.03.001 | journal = Dyes and Pigments | year = 2009 | volume = 82 | pages = 392–395 | issue = 3}} 4. ^{{cite journal | title = The Smallest and One of the Brightest. Efficient Preparation and Optical Description of the Parent Borondipyrromethene System |author1=I. J. Arroyo |author2=R. Hu |author3=G. Merino |author4=B. Z. Tang |author5=E. Peña-Cabrera | doi = 10.1021/jo901014w | journal = J. Org. Chem. | volume = 74 | pages = 5719–22 | year = 2009 | pmid=19572588 | issue = 15}} 5. ^{{cite journal|author=Zhong-Hua Pan|author2=Geng-Geng Luo|author3=Jing-Wei Zhou|author4=Jiu-Xu Xia|author5=Kai Fang|author6=Rui-Bo Wu|title=A simple BODIPY-aniline-based fluorescent chemosensor as multiple logic operations for the detection of pH and CO2 gas |doi=10.1039/C4DT00395K|journal=Dalton Trans.|volume=43|issue=22|year=2014|page=8499}} 6. ^1 2 3 {{Cite journal|last=Burgess|first=Kevin|date=October 2007|title=BODIPY Dyes and Their Derivatives: Syntheses and Spectroscopic Properties|journal=Chemical Reviews|volume=107|issue=11|pages=4891–4932|doi=10.1021/cr078381n|pmid=17924696}} 7. ^{{Cite web | url=http://www.b2b.invitrogen.com/site/us/en/home/References/Molecular-Probes-The-Handbook/Nucleic-Acid-Detection-and-Genomics-Technology/Labeling-Oligonucleotides-and-Nucleic-Acids.html | title=Antibodies - US}} External links
3 : Fluorescent dyes|Pyrroles|Organoboron compounds |
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