The Smallest and One of the Brightest. Efficient Preparation and Optical Description of the Parent Borondipyrromethene System

Arroyo, Ismael J.; Hu, Rongrong; Merino, Gabriel; Tang, Ben Zhong; Peña‐Cabrera, Eduardo

doi:10.1021/jo901014w

Cited by 167 publications

(142 citation statements)

References 47 publications

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“…In both cases, abs(max) is more red-shifted in the more polarizable solvents toluene and chlorobenzene. In contrast, the values of abs(max) of 8-Ph (with a phenyl substituent at the meso-position) are blue-shifted in relation to those of 2-Ph and 3-Ph and are close to those of unsubstituted boron dipyrromethene, 3,[22][23][24] ranging from 489 nm in acetonitrile to 497 nm in toluene and chlorobenzene: the solvent dependence correlating with the refractive index. This absorption energy range is in good agreement with that of other BODIPYs substituted at the mesoposition with a weak electron acceptor or donor.…”

Section: Spectroscopic and Photophysical Propertiesmentioning

confidence: 82%

“…19 Boron dipyrromethenes, modified at the meso-position with strong electron withdrawing groups, possess large red shifts, [20][21] because the LUMO is highly stabilized 3 compared to unsubstituted BODIPY. 3,[22][23][24] In contrast, electron donating groups at the meso-position cause a blue-shift in the absorption and emission spectra, while keeping high fluorescence quantum yields and lifetimes. [25][26][27][28] Certain modifications at the meso-position may result in almost nonfluorescent compounds, as for meso-alkenyl- 29 or meso-formylBODIPYs.…”

Section: Introductionmentioning

confidence: 99%

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Effect of the substitution position (2, 3 or 8) on the spectroscopic and photophysical properties of BODIPY dyes with a phenyl, styryl or phenylethynyl group

et al. 2016

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Noël (2016) Effect of the substitution position (2, 3 or 8) on the spectroscopic and photophysical properties of BODIPY dyes with a phenyl, styryl or phenylethynyl group. RSC Advances, 6 . pp. 102899-102913. ISSN 2046-2069 Access from the University of Nottingham repository: http://eprints.nottingham.ac.uk/37842/1/Ph%20Ethyn%20Styryl%20BODIPYs%20-%20Accepted%20Manuscript.pdf Copyright and reuse:The Nottingham ePrints service makes this work by researchers of the University of Nottingham available open access under the following conditions. This article is made available under the University of Nottingham End User licence and may be reused according to the conditions of the licence. For more details see: http://eprints.nottingham.ac.uk/end_user_agreement.pdf A note on versions:The version presented here may differ from the published version or from the version of record. If you wish to cite this item you are advised to consult the publisher's version. Please see the repository url above for details on accessing the published version and note that access may require a subscription.For more information, please contact eprints@nottingham. ABSTRACT. A very active branch of organic chemistry is putting great effort in tailoring fluorescent dyes for a myriad of applications, from technological to bioanalytical and biomedical applications. Among the major families of fluorophores, those derived from 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY dyes) are undergoing a recent boost thanks to the simplicity and robustness of the chemistry involved. The BODIPY core can be modified with numerous side groups, the 8-position being a modification place with important effects on the spectroscopic and photophysical properties of the resulting dyes. Likewise, previous work has shown that the addition of groups attached at the 3-and 2-positions can result in dyes with very different properties. Herein, we generalize the effect of the substituent side groups by studying nine BODIPY dyes substituted with a phenyl, styryl or phenylethynyl moiety at the 2-, 3-or 8-position of the BODIPY scaffold. Within the class of phenyl-or phenylethynyl-substituted dyes, substitution at the 2-position always leads to dyes with the broadest bandwidths and the largest Stokes shifts. We investigate the solvent effect on the spectroscopic properties of the dyes, using four empirical solvent scales (dipolarity, polarizability, acidity and basicity: Catalán, J. Phys. Chem., 2009, 113, 5951). These analyses identify solvent dipolarity and polarizability as critical parameters accounting for the observed solvent-dependent shifts of the absorption and emission maxima. Finally, time-dependent density functional theory calculations provide insights into the structural and energetic issues concerning the spectroscopic properties of these fluorophores.KEYWORDS: Fluorescent dyes, solvent effect, Catalán solvent scales, quantum chemical calculations TOCUnderstanding the spectroscopic properties of BODIPY dyes for a rationale design of tailored fluorescent ...

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Section: Spectroscopic and Photophysical Propertiesmentioning

confidence: 82%

Section: Introductionmentioning

confidence: 99%

Effect of the substitution position (2, 3 or 8) on the spectroscopic and photophysical properties of BODIPY dyes with a phenyl, styryl or phenylethynyl group

et al. 2016

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“…The only element in the compound with two isotopes of comparable abundance is boron. The heavier isotope B accounts for 80 % of the natural abundance; the lighter isotope 10 B accounts for 20 %. If this is the cause for the band shape, the spectrum should be the superposition of twice the identical band, as shown in Equation (1):…”

Section: Deconvolution Of Rotational Line Shapementioning

confidence: 99%

High‐Resolution Electronic Spectroscopy of the BODIPY Chromophore in Supersonic Beam and Superfluid Helium Droplets

et al. 2011

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We present the fluorescence excitation and dispersed emission spectra of the parent compound of the boron dipyrromethene (BODIPY) dye class measured in a supersonic beam and isolated in superfluid helium nanodroplets. The gas-phase spectrum of the isolated molecules displays many low-frequency transitions that are assigned to a symmetry-breaking mode with a strongly nonharmonic potential, presumably the out-of-plane wagging mode of the BF(2) group. The data are in good agreement with transition energies and Franck-Condon factors calculated for a double minimum potential in the upper electronic state. The corresponding transitions do not appear in the helium droplet. This is explained with the quasi-rigid first layer of helium atoms attached to the dopant molecule by van der Waals forces. The spectral characteristics are those of a cyanine dye rather than that of an aromatic chromophore.

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“…Boron dipyrromethene dyes (4,4-difluoro-4-bora-3a,4a-diazas-indacene dyes, 15 often called 'BODIPY' or 'BDP') shown in Fig. 2 can be regarded as being one of the most frequently investigated fluorophores during the first decade of the 21st century, as indicated by the publication of several review articles.…”

Section: Nir Fluorophores Based On Bodipy 2·1 Summary Of Bodipy Fluormentioning

confidence: 99%

New Trends in Near-Infrared Fluorophores for Bioimaging

2014

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The Smallest and One of the Brightest. Efficient Preparation and Optical Description of the Parent Borondipyrromethene System

Cited by 167 publications

References 47 publications

Effect of the substitution position (2, 3 or 8) on the spectroscopic and photophysical properties of BODIPY dyes with a phenyl, styryl or phenylethynyl group

Effect of the substitution position (2, 3 or 8) on the spectroscopic and photophysical properties of BODIPY dyes with a phenyl, styryl or phenylethynyl group

High‐Resolution Electronic Spectroscopy of the BODIPY Chromophore in Supersonic Beam and Superfluid Helium Droplets

New Trends in Near-Infrared Fluorophores for Bioimaging

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