Syntheses and Spectral Properties of Functionalized, Water-Soluble BODIPY Derivatives

Han, Junyan; Nguyen, Binh T.; Burgess, Kevin

doi:10.1021/jo702463f

Cited by 206 publications

(126 citation statements)

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“…Alternatively, we employed a recently developed protocol that enabled us to produce the dichloro-substituted BODIPY D (Scheme 3). [16,17] It has been established previously that replacement of both chloro groups by alkynyl functions can be brought about in the presence of palladium(0) catalysts. [17,18] In this specific case, the phenyliodo moieties in the BODIPY series B and C had to be replaced by the less reactive phenylbromo group, and the two methyl groups in the 1,7-positions had to be omitted to avoid steric crowding.…”

Section: Resultsmentioning

confidence: 99%

“…[16,17] It has been established previously that replacement of both chloro groups by alkynyl functions can be brought about in the presence of palladium(0) catalysts. [17,18] In this specific case, the phenyliodo moieties in the BODIPY series B and C had to be replaced by the less reactive phenylbromo group, and the two methyl groups in the 1,7-positions had to be omitted to avoid steric crowding. After some trials, the mono-and disubstituted alkynylpyrene derivatives PyD and Py 2 D were isolated from D as starting material.…”

Section: Resultsmentioning

confidence: 99%

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Quasi‐One‐Dimensional Electronic Systems Formed from Boron Dipyrromethene (BODIPY) Dyes

Ziessel

Rihn

Harriman

2010

Chemistry A European J

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Synthetic strategies have been devised that allow the rational design and isolation of highly coloured boron dipyrromethene (BODIPY) dyes that absorb across much of the visible region. Each dye has an aryl polycycle (usually pyrene or perylene) connected to the central BODIPY core through a conjugated tether at the 3,5-positions. Both mono- and difunctionalised derivatives are accessible, in certain cases containing both pyrene and perylene residues. For all new compounds, the photophysical properties have been recorded in solution at ambient temperature and in a glassy matrix at 77 K. The presence of the aryl polycycle(s) affects the absorption and emission maxima of the BODIPY nucleus, thereby confirming that these units are coupled electronically. Indeed, the band maxima and oscillator strengths depend on the conjugation length of the entire molecule, whereas there is no sign of fluorescence from the polycycle. As a consequence, the radiative rate constant tends to increase with each added appendage. The nature of the linkage (styryl, ethenyl, or ethynyl) also exerts an effect on the photophysical properties and, in particular, the absorption spectrum is perturbed in the region of the aryl polycycle. The perylene-containing BODIPY derivatives absorb over a wide spectral range and emit in the far-red region in almost quantitative yield. A notable exception to this generic behaviour is provided by the anthracenyl derivative, which exhibits charge-transfer absorption and emission spectra in weakly polar media at ambient temperature. Regular BODIPY-like behaviour is restored in a glassy matrix at 77 K. Overall, these new dyes represent an important addition to the range of strongly absorbing and emitting reagents that could be used as solar concentrators.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Quasi‐One‐Dimensional Electronic Systems Formed from Boron Dipyrromethene (BODIPY) Dyes

Ziessel

Rihn

Harriman

2010

Chemistry A European J

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“…Water-soluble BODIPY compounds [21][22][23][24] should have attractive applications in biological and medical analyses and A C C E P T E D M A N U S C R I P T ACCEPTED MANUSCRIPT 4 diagnostics. Bard and his collaborators have been pioneers in the study of the electrochemiluminescence of BODIPY dyes [25,26], especially for the ECL watersoluble BODIPYs [27].…”

Section: Introductionmentioning

confidence: 99%

Comparison study of electrochemiluminescence of boron-dipyrromethene (BODIPY) dyes in aprotic and aqueous solutions

Chauhan

Chu

Yan

et al. 2016

Journal of Electroanalytical Chemistry

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“…Aromatic sulfonation is an excellent method for enhancing the water solubility of lipophilic aromatic compounds, and has been applied to create water soluble dyes and polymers [1][2][3] , and to enhance prototropic exchange in various solid-state ionic materials. 4 Classically, aryl sulfonation occurs under forcing electrophilic conditions and the methods used for CH functionalisation are generally not suitable for multifunctional compounds with electron-rich or nucleophilic groups.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of meta and para-substituted aromatic sulfonate derivatives of polydentate phenylazaphosphinate ligands: enhancement of the water solubility of emissive europium(iii) EuroTracker® dyes

2014

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Publisher's copyright statement:Additional information: Use policyThe full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-pro t purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.Please consult the full DRO policy for further details. Results and DiscussionThe target complexes ( Fig. 1) include three strongly absorbing and equivalent chromophores, in which there is meta or para-sulfonic acid substituent in the phenyl ring of the phosphinate moiety. The sulfonation of this position was not expected to perturb the chromophore characteristics significantly, as the phosphorus oxygen bond and the aryl groups to which it is attached are not strongly conjugated, unlike a trigonal amide or carboxylate substituent.Previous X-ray analysis studies of these phenylphosphinate lanthanide complexes have revealed that the phenyl rings are oriented in the same direction, away from the plane of the 9-N 3 ring, and with the same relative configuration at phosphorus. 13,15,16 These structural studies also confirmed that the phosphorus-oxygen double bond lies out of the plane of the aryl rings. A simple retrosynthetic analysis suggests the intermediacy of a 2,4,6-trisubstituted pyridine, with a 4-Br group, allowing a Sonogashira coupling reaction to an arylalkyne in a final ligand assembly step. the P centres respectively, as deduced by X-ray and CD studies on related systems. [13][14][15][16] OBC 2014 Delbianco 3In order to form the C-P bond, a palladium-catalysed reaction was envisaged, allowing insertion of a 2-pyridyl group into the P-H bond of a phenylphosphinic ester, bearing a suitably protected sulfonate group. Following the studies of Miller, 6a the behaviour of the trifluoroethyl and phenylsulfonate esters as protecting groups for the sulfonic acid moiety was examined; each ester was derived from 3 or 4-bromo-phenylsulfonyl chloride (Scheme 1).Palladium-catalysed coupling between the aryl bromide and anilinium hypophosphite proceeded in 70% yield for the trifluoroethyl ester, but failed with the phenyl ester, probably due to competitive insertion into the O-Ph bond. In this reaction, the added aminopropyltriethoxysilane serves as a base in the Pd-catalysed reaction, and enables the esterification of the phosphinic acid in situ. 17-19 Scheme 1The di-esters 3 and 4 were used in coupling reactions with 2-bromo-4-nitro-6-methyl pyridine in degassed toluene using Cl 2 Pd[bis(diphenylphosphino)ferrocene] as the catalyst to give the phosphinate esters 5 and 6 (Scheme 2). Bromination with neat acetyl bromide followed by reesterification of the phosphinic acid group with HC(OEt) 3 allowed the isolation of intermediates 7 and 8 in 77 and 81 % yield respectively. Treatme...

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Syntheses and Spectral Properties of Functionalized, Water-Soluble BODIPY Derivatives

Cited by 206 publications

References 38 publications

Quasi‐One‐Dimensional Electronic Systems Formed from Boron Dipyrromethene (BODIPY) Dyes

Quasi‐One‐Dimensional Electronic Systems Formed from Boron Dipyrromethene (BODIPY) Dyes

Comparison study of electrochemiluminescence of boron-dipyrromethene (BODIPY) dyes in aprotic and aqueous solutions

Synthesis of meta and para-substituted aromatic sulfonate derivatives of polydentate phenylazaphosphinate ligands: enhancement of the water solubility of emissive europium(iii) EuroTracker® dyes

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