User:Circador/BODIPY
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[edit]Lead
[edit]BODIPY is the technical common name of a chemical compound with formula C
9H
7BN
2F
2, whose molecule consists of a boron difluoride group BF
2 joined to a dipyrromethene group C
9H
7N
2; specifically, the compound 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene in the IUPAC nomenclature.[1] The common name is an abbreviation for "boron-dipyrromethene". It is a red crystalline solid, stable at ambient temperature, soluble in methanol.[1]
The compound itself was isolated only in 2009,[2][1][3] but many derivatives—formally obtained by replacing one or more hydrogen atoms by other functional groups—have been known since 1968, and comprise the important class of BODIPY dyes.[4] These organoboron compounds have attracted much interest as fluorescent dyes and markers in biological research.[1]
Derivatives
[edit]
The BODIPY core has a rich derivative chemistry due to the high tolerance for substitutions in the pyrrole and aldehyde (or acyl chloride) starting materials.[7]
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.[7]
The two fluorine atoms on the boron atom can be replaced, during or after synthesis, by other strong nucleophilic reagents, such as lithiated alkyne or aryl species,[7] chlorine,[8] methoxy,[8] or a divalent "strap".[9] The reaction is catalysed by BBr3 or SnCl4.[10]
References
[edit]- ^ a b c d K. Tram; H. Yan; H. A. Jenkins; S. Vassiliev; D. Bruce (2009). "The synthesis and crystal structure of unsubstituted 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY)". Dyes and Pigments. 82 (3): 392–395. doi:10.1016/j.dyepig.2009.03.001.
- ^ A. Schmitt; B. Hinkeldey; M. Wild; G. Jung (2009). "Synthesis of the Core Compound of the BODIPY Dye Class: 4,4′-Difluoro-4-bora-(3a,4a)-diaza-s-indacene". J. Fluoresc. 19 (4): 755–759. doi:10.1007/s10895-008-0446-7. PMID 19067126. S2CID 7012021.
- ^ I. J. Arroyo; R. Hu; G. Merino; B. Z. Tang; E. Peña-Cabrera (2009). "The Smallest and One of the Brightest. Efficient Preparation and Optical Description of the Parent Borondipyrromethene System". J. Org. Chem. 74 (15): 5719–22. doi:10.1021/jo901014w. PMID 19572588.
- ^ Alfred Treibs und Franz-Heinrich Kreuzer. Difluorboryl-Komplexe von Di- und Tripyrrylmethenen. Justus Liebigs Annalen der Chemie 1968, 718 (1): 208-223.
- ^ Aurore Loudet and Kevin Burgess (2007): "BODIPY dyes and their derivatives: Syntheses and spectroscopic properties". Chemical Reviews, volume 107, issue 11, pages 4891–4932. doi:10.1021/cr078381n
- ^ Zhong-Hua Pan; Geng-Geng Luo; Jing-Wei Zhou; Jiu-Xu Xia; Kai Fang; Rui-Bo Wu (2014). "A simple BODIPY-aniline-based fluorescent chemosensor as multiple logic operations for the detection of pH and CO2 gas". Dalton Transactions. 43 (22): 8499–507. doi:10.1039/C4DT00395K. PMID 24756338.
- ^ a b c Burgess, Kevin (October 2007). "BODIPY Dyes and Their Derivatives: Syntheses and Spectroscopic Properties". Chemical Reviews. 107 (11): 4891–4932. doi:10.1021/cr078381n. PMID 17924696.
- ^ a b Groves, Brandon R.; Crawford, Sarah M.; Lundrigan, Travis; Matta, Chérif F.; Sowlati-Hashjin, Shahin; Thompson, Alison (2013). "Synthesis and characterisation of the unsubstituted dipyrrin and 4,4-dichloro-4-bora-3a,4a-diaza-s-indacene: Improved synthesis and functionalisation of the simplest BODIPY framework". Chem. Commun. 49 (8): 816–818. doi:10.1039/c2cc37480c. PMID 23235887.
- ^ Stachelek, Patrycja; Alsimaree, Abdulrahman A.; Alnoman, Rua B.; Harriman, Anthony; Knight, Julian G. (2017-03-16). "Thermally-Activated, Delayed Fluorescence in O,B,O- and N,B,O-Strapped Boron Dipyrromethene Derivatives". The Journal of Physical Chemistry A. 121 (10): 2096–2107. Bibcode:2017JPCA..121.2096S. doi:10.1021/acs.jpca.6b11131. ISSN 1089-5639. PMID 28245114.
- ^ Sirbu, Dumitru; Benniston, Andrew C.; Harriman, Anthony (2017-04-07). "One-Pot Synthesis of a Mono-O,B,N-strapped BODIPY Derivative Displaying Bright Fluorescence in the Solid State". Organic Letters. 19 (7): 1626–1629. doi:10.1021/acs.orglett.7b00435. ISSN 1523-7060. PMID 28319396.