Anthracene-Fused BODIPYs as Near-Infrared Dyes with High Photostability

Zeng, Lintao; Jiao, Chongjun; Huang, Xiaobo; Huang, Kuo‐Wei; Chin, Wee-Shong; Wu, Jishan

doi:10.1021/ol202493c

Cited by 89 publications

(33 citation statements)

References 59 publications

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“…6 Furthermore, aryl-fused BODIPYs with flattened structures tend to promote solid state fluorescence. 7 As a consequence, a significant number of benzo-[ a ] 8 and [ b ] 3c, 6, 9 fused, meso- (8) - aryl-fused 10 and B,O-chelated 11 BODIPYs have been reported in the last decade. However, a main challenge remains in the case of 8-aryl substituted BODIPYS, due to the rotation of the meso (8)-aryl group (e.g.…”

Section: Introductionmentioning

confidence: 99%

Enhanced Hypsochromic Shifts, Quantum Yield, and π–π Interactions in a meso,β-Heteroaryl-Fused BODIPY

et al. 2017

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We report the synthesis and investigation of an unprecedented 8-heteroaryl-fused BODIPY 4. This compound exhibits enhanced π-π stacking in the solid state, unusually large blue-shifts in the absorbance and emission spectra, and higher quantum yield than its unfused precursor; DFT calculations suggest a small energy gap for 4, and strong electronic communication between the 8-OPh and the BODIPY core.

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Section: Introductionmentioning

confidence: 99%

Enhanced Hypsochromic Shifts, Quantum Yield, and π–π Interactions in a meso,β-Heteroaryl-Fused BODIPY

et al. 2017

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“…For instance, fusing rigid -conjugated carbocycles to the BODIPY core results in near-infrared emitting dyes. [13][14][15][16] Modification at the 8-(or meso-) position (Chart 1) results in a variety of substituent-promoted effects, as quantum chemical calculations have demonstrated the presence of a node in the HOMO at this position and a significant increase of the electron density upon excitation. 17 Alkylation at the meso-position usually has a mild effect, resulting in boron dipyrromethenes with emission maxima around 500 nm and large fluorescence quantum yield values.…”

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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“…Moreover, it is notable that the Stokes shift has increased from 294 cm À1 (8 nm) for BODIPY 1 to 1425 cm À1 (53 nm) for BODIPY 2, perhaps due to the formation of dimer [10c] and the desymmetrization of BODIPY 2 [18]. The fluorescence quantum yield (40% in chloroform) of BODIPY 2 is much higher than that (0.4% in chloroform) of BODIPY 1 and also higher than that of other "zig-zag" ring fused BODIPY [14]. This can be attributed to the inhibition of the free rotation of anthryl group and less nonirradiative energy loss [10b].…”

Section: Resultsmentioning

confidence: 99%

“…In order to obtain large Stokes shifts, a number of approaches have been reported, such as (a) formation of oligomers [10]; (b) construction of tandem systems [11]; (c) photoinduced intramolecular charge transfer [12] and (d) excited state proton transfer [13]. Some strategies, although effective, are usually structurally complex and require significant synthetic effort [14].…”

Section: Introductionmentioning

confidence: 99%

Asymmetric anthracene-fused BODIPY dye with large Stokes shift: Synthesis, photophysical properties and bioimaging

et al. 2016

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Anthracene-Fused BODIPYs as Near-Infrared Dyes with High Photostability

Cited by 89 publications

References 59 publications

Enhanced Hypsochromic Shifts, Quantum Yield, and π–π Interactions in a meso,β-Heteroaryl-Fused BODIPY

Enhanced Hypsochromic Shifts, Quantum Yield, and π–π Interactions in a meso,β-Heteroaryl-Fused BODIPY

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

Asymmetric anthracene-fused BODIPY dye with large Stokes shift: Synthesis, photophysical properties and bioimaging

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