New difluoro-boradiazaindacene shaped with gallate platforms

Ziessel, Raymond; Bonardi, Laure; Retailleau, Pascal; Camerel, Franck

doi:10.1016/j.crci.2008.01.005

Cited by 5 publications

(2 citation statements)

References 68 publications

(49 reference statements)

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“…4 A very active branch of scientific development is putting great effort in fine-tuning the BODIPY properties by introducing suitable chemical groups onto the central core. As a result, the BODIPY family is expanding constantly and has found applications in wide-ranging fields, from technological (organic light-emitting diodes, [5][6][7] dye-sensitized solar cells [8][9] ) to analytical and in vivo imaging applications. [10][11] Recent advances in organic synthesis have expanded the possibilities of controlled modification of the BODIPY moiety, including substitution by tailored groups at every position of the core.…”

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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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: 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 dipyrrin (dipyrromethene) boron complex 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) has recently attracted considerable attention due to its narrow and intense absorption and emission, [1][2][3][4] although the first dipyrrins as a bidentate ligand with the two nitrogen atoms (N 2 dipyrrins in this Account) and the BODIPYs were reported by Treibs and Kreuzer in 1968. 5 The excellent photophysical properties of BODIPY derivatives have been utilized for fluorescence tag and probe molecules, [6][7][8][9][10][11][12] fluorescence sensors, 8,[10][11][12][13][14] bioimaging, 9,11,12,15,16 electrogenerated chemiluminescence dye, 17 and possible applications such as organic thin-film transistors, 18 laser dye, 19 OLED (organic lightemitting diode), 17,[20][21][22][23] photodynamic therapy, [24][25][26] solar cells, 19,[27][28][29] polymer photonics devices, 30 etc. There are many reports concerning the derivatization of the N 2bidentate dipyrrins by attaching a variety of substituents, extending the -planar dipyrrin nucleus, and introducing a nitrogen atom into the dipyrrin framework, then preparing the corresponding boron complexes.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Functions of Oligomeric and Multidentate Dipyrrin Derivatives and their Complexes

Chiba¹,

Nakamura²,

Matsuoka³

et al. 2020

Synlett

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The dipyrrin–metal complexes and especially the boron complex 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) have recently attracted considerable attention because of their interesting properties and possible applications. We have developed two unique and useful ways to extend versatility and usefulness of the dipyrrin complexes. The first one is the linear and macrocyclic oligomerization of the BODIPY units. These arrangements of the B–F moieties of the oligomerized BODIPY units provide sophisticated functions, such as unique recognition ability toward cationic guest, associated with changes in the photophysical properties by utilizing unprecedented interactions between the B–F and a cationic species. The second one is introduction of additional ligating moieties into the dipyrrin skeleton. The multidentate N2Ox dipyrrin ligands thus obtained form a variety of complexes with 13 and 14 group elements, which are difficult to synthesize using the original N2 dipyrrin derivatives. Interestingly, these unique complexes exhibit novel structures, properties, and functions such as guest recognition, stimuli-responsive structural conversion, switching of the optical properties, excellent stability of the neutral radicals, etc. We believe that these multifunctional dipyrrin complexes will advance the basic chemistry of the dipyrrin complexes and develop their applications in the materials and medicinal chemistry fields.1 Introduction2 Linear Oligomers of Boron–Dipyrrin Complexes3 Cyclic Oligomers of Boron–Dipyrrin Complexes4 A Cyclic Oligomer of Zinc–Dipyrrin Complexes5 Group 13 Element Complexes of N2Ox Dipyrrins6 Chiral N2 and N2Ox Dipyrrin Complexes7 Group 14 Element Complexes of N2O2 Dipyrrins8 Other N2O2 Dipyrrin Complexes with Unique Properties and Functions9 Conclusion

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Synthesis of BODIPY dyes through postfunctionalization of the boron dipyrromethene core

Boens

Verbelen

Ortiz

et al. 2019

Coordination Chemistry Reviews

299

173

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New difluoro-boradiazaindacene shaped with gallate platforms

Cited by 5 publications

References 68 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

Synthesis and Functions of Oligomeric and Multidentate Dipyrrin Derivatives and their Complexes

Synthesis of BODIPY dyes through postfunctionalization of the boron dipyrromethene core

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