358:
692:. They are relatively insensitive to the polarity and pH of their environment and are reasonably stable to physiological conditions. Small modifications to their structures enable tuning of their fluorescence characteristics. BODIPY dyes 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.
622:
722:, 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
27:
631:
953:
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
601:
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
506:
In its crystalline solid form, the core BODIPY is almost, but not entirely, planar and symmetrical; except for the two fluorine atoms, that lie on the perpendicular bisecting plane. Its bonding can be explained by assuming a formal negative charge on the boron atom, and a formal positive charge on
734:
The advantages of BODIPY are their low photodegradation, low toxicity and polarity, high biocompatibility, charge neutrality, and high fluorescence quantum yield, all of which make BODIPY effective markers. BODIPY conjugates are widely studied as potential sensors and for labelling biobjects (e.g.
1325:
Guseva, Galina B.; Antina, Elena V.; Berezin, Mikhail B.; Ksenofontov, Alexander A.; Bocharov, Pavel S.; Smirnova, Anastassia S.; Pavelyev, Roman S.; Gilfanov, Ilmir R.; Pestova, Svetlana V.; Izmest'ev, Evgeny S.; Rubtsova, Svetlana A.; Kayumov, Airat R.; Kiselev, Sergei V.; Azizova, Zulfiya R.;
1439:
Sirbu, Dumitru; Luli, Saimir; Leslie, Jack; Oakley, Fiona; Benniston, Andrew C. (2019-05-17). "Enhanced in vivo
Optical Imaging of the Inflammatory Response to Acute Liver Injury in C57BL/6 Mice Using a Highly Bright Near-Infrared BODIPY Dye".
625:
IUPAC atom numbering for substitutions on the BODIPY core. Positions 3 and 5 are also commonly called "α"; 1,2,6,7 are called "β"; and 8 is called "meso". Note that the numbering does not match the numbering on the parent 2,2'-dipyrromethene
581:
The dipyrromethene precursors are accessed from a suitable pyrrole derivatives by several methods. Normally, one alpha-position in employed pyrroles is substituted and the other is free. Condensation of such pyrrole, often available from
1048:
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".
1012:
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".
1381:
Kaufman, Nichole E. M.; Meng, Qianli; Griffin, Kaitlin E.; Singh, Sitanshu S.; Dahal, Achyut; Zhou, Zehua; Fronczek, Frank R.; Mathis, J. Michael; Jois, Seetharama D.; Vicente, M. Graça H. (2019-04-11).
859:
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".
1384:"Synthesis, Characterization, and Evaluation of Near-IR Boron Dipyrromethene Bioconjugates for Labeling of Adenocarcinomas by Selectively Targeting the Epidermal Growth Factor Receptor"
1100:
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".
786:
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)".
1328:"Conjugate of meso-carboxysubstituted-BODIPY with thioterpenoid as an effective fluorescent probe: Synthesis, structure, spectral characteristics, and molecular docking"
357:
656:
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,
1276:
Cooper, Mark S.; Szeto, Daniel P.; Sommers-Herivel, Greg; Topczewski, Jacek; Solnica-Krezel, Lila; Kang, Hee-Chol; Johnson, Iain; Kimelman, David (February 2005).
475:
nomenclature. The common name is an abbreviation for "boron-dipyrromethene". It is a red crystalline solid, stable at ambient temperature, soluble in methanol.
638:
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.
239:
816:
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".
1680:
Kim, Ha Na; Ren, Wen Xiu; Kim, Jong Seung; Yoon, Juyoung (2012). "Fluorescent and colorimetric sensors for detection of lead, cadmium, and mercury ions".
893:
Alfred Treibs und Franz-Heinrich
Kreuzer. Difluorboryl-Komplexe von Di- und Tripyrrylmethenen. Justus Liebigs Annalen der Chemie 1968, 718 (1): 208-223.
591:
103:
742:. In recent years, BODIPY derivatives are also being explored as photosensitizers for applications in photodynamic therapy and photocatalysis.
1610:
Lu, Hua; Mack, John; Yang, Yongchao; Shen, Zhen (2014). "Structural modification strategies for the rational design of red/NIR region BODIPYs".
699:(peaking at 503 nm) and a broad emission band from about 480 to 580 nm (peaking at 512 nm), with a fluorescence lifetime of 7.2
1491:
Kowada, Toshiyuki; Maeda, Hiroki; Kikuchi, Kazuya (2015). "BODIPY-based probes for the fluorescence imaging of biomolecules in living cells".
1526:
Ni, Yong; Wu, Jishan (2014). "Far-red and near infrared BODIPY dyes: Synthesis and applications for fluorescent pH probes and bio-imaging".
575:
608:
214:
578:(DBU). The difficulty of the synthesis was due to instability of the usual dipyrromethene precursor, rather than of BODIPY itself.
641:
Hydrogen atoms at the 2 and 6 positions of the cyclic core can be displaced by halogen atoms using succinimide reagents such as
653:- which allows for further post-functionalisation through palladium coupling reactions with boronate esters, tin reagents etc.
1192:"Carboxyl BODIPY Dyes from Bicarboxylic Anhydrides: One-Pot Preparation, Spectral Properties, Photostability, and Biolabeling"
1882:
1278:"Visualizing morphogenesis in transgenic zebrafish embryos using BODIPY TR methyl ester dye as a vital counterstain for GFP"
345:
991:
Aurore Loudet and Kevin
Burgess (2007): "BODIPY dyes and their derivatives: Syntheses and spectroscopic properties".
703:. Its fluorescence quantum yield is near 1, greater than that of substituted BODIPY dyes and comparable to those of
684:
with unique properties. They strongly absorb UV-radiation and re-emit it in very narrow frequency spreads, with high
1716:
1872:
478:
The compound itself was isolated only in 2009, but many derivatives—formally obtained by replacing one or more
913:
Burgess, Kevin (October 2007). "BODIPY Dyes and Their
Derivatives: Syntheses and Spectroscopic Properties".
583:
739:
516:
155:
487:
1763:
1190:
Wang, Dongchuan; Fan, Jiangli; Gao, Xinqin; Wang, Bingshuai; Sun, Shiguo; Peng, Xiaojun (2009-10-16).
1728:
1645:
Roncali, Jean (2009). "Molecular Bulk
Heterojunctions: An Emerging Approach to Organic Solar Cells".
1339:
1250:
1058:
587:
39:
723:
642:
69:
1848:
1801:
1473:
1363:
1327:
1238:
841:
738:
Numerous BODIPY derivatives are being investigated as electroactive species for single-substance
646:
482:
atoms by other functional groups—have been known since 1968, and comprise the important class of
115:
26:
1239:"Single molecule fluorescence detection of BODIPY-FL molecules for monitoring protein synthesis"
1237:
Perronet, K.; Bouyer, P.; Westbrook, N.; Soler, N.; Fourmy, D.; Yoshizawa, S. (November 2007).
1877:
1840:
1793:
1744:
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1627:
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1543:
1508:
1465:
1457:
1421:
1403:
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1307:
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1211:
1172:
1164:
1125:
1117:
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833:
650:
520:
412:
369:
175:
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1411:
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1347:
1289:
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1203:
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1109:
1066:
1022:
996:
963:
922:
868:
825:
795:
415:
262:
79:
894:
680:
BODIPY and many of its derivatives have received attention recently for being fluorescent
590:
gives dipyrromethane, which is oxidized to dipyrromethene using a quinone oxidant such as
1732:
1343:
1254:
1062:
135:
1587:
1562:
1416:
1383:
430:
339:
1145:"Structural modification strategies for the rational design of red/NIR region BODIPYs"
621:
1866:
1852:
1805:
1367:
719:
685:
571:
524:
317:
200:
1477:
845:
715:
491:
1399:
1262:
799:
1819:
De
Bonfils, Paul; Péault, Louis; Nun, Pierrick; Coeffard, Vincent (2021-03-26).
1717:"Characterization of a BODIPY Dye as an Active Species for Redox Flow Batteries"
1113:
708:
595:
361:
Samples of halogenated BODIPY dyes in ambient lighting and fluorescing under UV
1779:
1351:
829:
735:
cell organelles) by exploiting its highly tunable optoelectronic properties.
700:
327:
299:
166:
1844:
1797:
1461:
1407:
1303:
1215:
1191:
1168:
1121:
1078:
1070:
704:
696:
695:
The unsubstituted BODIPY has a broad absorption band, from about 420 to 520
689:
1836:
1748:
1740:
1701:
1666:
1631:
1596:
1547:
1512:
1469:
1453:
1425:
1359:
1311:
1223:
1176:
1129:
1086:
1034:
975:
934:
880:
837:
1715:
Kosswattaarachchi, Anjula M.; Friedman, Alan E.; Cook, Timothy R. (2016).
607:
657:
515:
BODIPY and its derivatives can be obtained by reacting the corresponding
479:
1788:
1764:"Photosensitization and controlled photosensitization with BODIPY dyes"
1693:
1623:
1578:
1539:
1504:
1294:
1277:
1160:
1144:
1026:
967:
661:
634:
Molecular structure of 1,3,5,7-tetramethyl-8-phenyl-substituted BODIPY.
495:
187:
1821:"State of the Art of Bodipy-Based Photocatalysts in Organic Synthesis"
1658:
1207:
1000:
926:
872:
146:
1762:
Turksoy, Abdurrahman; Yildiz, Deniz; Akkaya, Engin U. (2019-01-15).
630:
338:
Except where otherwise noted, data are given for materials in their
1332:
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy
1770:. Novel and Smart Photosensitizers from Molecule to Nanoparticle.
629:
620:
472:
356:
223:
InChI=1S/C9H7BF2N2/c11-10(12)13-5-1-3-8(13)7-9-4-2-6-14(9)10/h1-7H
126:
102:
92:
602:
of dipyrromethenes is usually compromised by their instability.
681:
606:
664:, or a divalent "strap". The reaction is catalysed by BBr
1143:
Lu, Hua; Mack, John; Yang, Yongchao; Shen, Zhen (2014).
16:
Parent chemical compound of the BODYPY fluorescent dyes
714:BODIPY dyes are notable for their uniquely small
199:
1563:"New photosensitizers for photodynamic therapy"
586:, with an aromatic aldehyde in the presence of
78:
1561:Abrahamse, Heidi; Hamblin, Michael R. (2016).
718:, high, environment-independent fluorescence
711:, but fluorescence is lost above 50 °C.
8:
781:
987:
985:
948:
946:
944:
908:
906:
904:
902:
811:
809:
779:
777:
775:
773:
771:
769:
767:
765:
763:
761:
490:compounds have attracted much interest as
174:
18:
1787:
1586:
1415:
1293:
995:, volume 107, issue 11, pages 4891–4932.
48:-4λ-dipyrrolodiazaborinin-4-ylium-5-uide
757:
244:
219:
1326:Ostolopovskaya, Olga V. (March 2022).
1825:European Journal of Organic Chemistry
226:Key: GUHHEAYOTAJBPT-UHFFFAOYSA-N
154:
134:
7:
1528:Organic & Biomolecular Chemistry
1051:The Journal of Physical Chemistry A
190:
688:, mostly at wavelengths below 600
368:is the technical common name of a
14:
724:change of permanent dipole moment
1196:The Journal of Organic Chemistry
465:4,4-difluoro-4-bora-3a,4a-diaza-
289:
283:
274:
25:
411:, whose molecule consists of a
342:(at 25 °C , 100 kPa).
1768:Coordination Chemistry Reviews
1388:Journal of Medicinal Chemistry
268:
57:Dipyrrometheneboron difluoride
1:
1647:Accounts of Chemical Research
895:doi: 10.1002/jlac.19687180119
463:; specifically, the compound
280:
1400:10.1021/acs.jmedchem.8b01746
1263:10.1016/j.jlumin.2007.02.051
800:10.1016/j.dyepig.2009.03.001
1114:10.1021/acs.orglett.7b00435
576:1,8-diazabicycloundec-7-ene
507:one of the nitrogen atoms.
247:1(N2C=CC=C2C=C31=CC=C3)(F)F
1899:
726:upon excitation is small.
332:methanol, dichloromethane
304:191.98 g/mol
1780:10.1016/j.ccr.2017.09.029
1352:10.1016/j.saa.2021.120638
830:10.1007/s10895-008-0446-7
336:
255:
235:
210:
62:
54:
38:
33:
24:
1493:Chemical Society Reviews
1071:10.1021/acs.jpca.6b11131
1243:Journal of Luminescence
584:Knorr pyrrole synthesis
1837:10.1002/ejoc.202001446
1741:10.1002/cssc.201601104
1454:10.1002/cmdc.201900181
1282:Developmental Dynamics
730:Potential applications
635:
627:
611:
362:
312:red crystalline solid
1883:Organoboron compounds
633:
624:
610:
570:) in the presence of
360:
740:redox flow batteries
588:trifluoroacetic acid
494:dyes and markers in
40:Preferred IUPAC name
1733:2016ChSCh...9.3317K
1567:Biochemical Journal
1344:2022AcSpA.26820638G
1255:2007JLum..127..264P
1063:2017JPCA..121.2096S
1015:Dalton Transactions
517:2,2'-dipyrromethene
116:Beilstein Reference
21:
1694:10.1039/C1CS15245A
1624:10.1039/C4CS00030G
1579:10.1042/BJ20150942
1540:10.1039/c3ob42554a
1505:10.1039/C5CS00030K
1295:10.1002/dvdy.20252
1161:10.1039/C4CS00030G
1027:10.1039/C4DT00395K
968:10.1039/c2cc37480c
636:
628:
612:
363:
346:Infobox references
19:
1831:(12): 1809–1824.
1727:(23): 3317–3323.
1659:10.1021/ar900041b
1653:(11): 1719–1730.
1618:(13): 4778–4823.
1499:(14): 4953–4972.
1208:10.1021/jo901149y
1202:(20): 7675–7683.
1155:(13): 4778–4823.
1057:(10): 2096–2107.
1001:10.1021/cr078381n
927:10.1021/cr078381n
921:(11): 4891–4932.
873:10.1021/jo901014w
788:Dyes and Pigments
521:boron trifluoride
519:derivatives with
370:chemical compound
354:Chemical compound
352:
351:
104:Interactive image
1890:
1873:Fluorescent dyes
1857:
1856:
1816:
1810:
1809:
1791:
1759:
1753:
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1712:
1706:
1705:
1688:(8): 3210–3244.
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1394:(7): 3323–3335.
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1267:
1266:
1234:
1228:
1227:
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1108:(7): 1626–1629.
1097:
1091:
1090:
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1039:
1038:
1021:(22): 8499–507.
1009:
1003:
993:Chemical Reviews
989:
980:
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915:Chemical Reviews
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413:boron difluoride
410:
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391:
390:
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381:
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276:
270:
263:Chemical formula
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1560:
1559:
1555:
1534:(23): 3774–91.
1525:
1524:
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1490:
1489:
1485:
1448:(10): 995–999.
1438:
1437:
1433:
1380:
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1319:
1275:
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1102:Organic Letters
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867:(15): 5719–22.
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1573:(4): 347–364.
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1288:(2): 359–368.
1268:
1249:(1): 264–268.
1229:
1182:
1149:Chem. Soc. Rev
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1092:
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1004:
981:
962:(8): 816–818.
940:
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886:
851:
824:(4): 755–759.
805:
794:(3): 392–395.
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720:quantum yields
686:quantum yields
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431:dipyrromethene
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340:standard state
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1186:
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1123:
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1096:
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623:
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579:
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572:triethylamine
526:
525:diethyl ether
522:
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510:
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318:Melting point
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464:
429:joined to a
365:
364:
63:Identifiers
55:Other names
45:
1789:11693/52868
1721:ChemSusChem
1442:ChemMedChem
818:J. Fluoresc
709:fluorescein
617:Derivatives
596:p-chloranil
492:fluorescent
488:organoboron
484:BODIPY dyes
309:Appearance
256:Properties
136:CHEBI:51107
80:138026-71-8
1867:Categories
1338:: 120638.
752:References
498:research.
496:biological
328:Solubility
300:Molar mass
167:ChemSpider
91:3D model (
70:CAS Number
1853:233683967
1845:1434-193X
1806:104018445
1798:0010-8545
1774:: 47–64.
1462:1860-7179
1408:0022-2623
1368:244408920
1304:1058-8388
1216:0022-3263
1169:0306-0012
1122:1523-7060
1079:1089-5639
705:rhodamine
626:molecule.
527:complex (
511:Synthesis
502:Structure
469:-indacene
1878:Pyrroles
1749:27863048
1702:22184584
1667:19580313
1632:24733589
1597:26862179
1548:24781214
1513:25801415
1478:85544665
1470:30920173
1426:30835998
1360:34840052
1312:15614774
1224:19772337
1177:24733589
1130:28319396
1087:28245114
1035:24756338
976:23235887
935:17924696
881:19572588
838:19067126
658:chlorine
486:. These
480:hydrogen
201:25058173
176:19572352
121:8139995
1729:Bibcode
1588:4811612
1417:6693348
1340:Bibcode
1251:Bibcode
1059:Bibcode
846:7012021
668:or SnCl
662:methoxy
471:in the
322:450 °C
188:PubChem
20:BODIPY
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240:SMILES
147:ChEMBL
34:Names
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1802:S2CID
1474:S2CID
1364:S2CID
842:S2CID
473:IUPAC
416:group
215:InChI
127:ChEBI
93:JSmol
1841:ISSN
1829:2021
1794:ISSN
1745:PMID
1698:PMID
1663:PMID
1628:PMID
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1466:PMID
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649:and
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651:NIS
647:NBS
643:NCS
594:or
592:DDQ
574:or
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