Carboxylates versus Fluorines: Boosting the Emission Properties of Commercial BODIPYs in Liquid and Solid Media

Durán-Sampedro, Gonzalo; Agarrabeitia, Antonia R.; Cerdán, Luis; Pérez‐Ojeda, M. Eugenia; Costela, Á.; García‐Moreno, Inmaculada; Esnal, Ixone; Bañuelos, Jorge; López‐Arbeloa, Íñigo; Ortiz, María J.

doi:10.1002/adfm.201300198

Cited by 62 publications

(56 citation statements)

References 84 publications

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“…On the other hand, we had also observed that, in the case of O -BODIPYs involving carboxyl units attached to the boron, those having electron-withdrawing (EW) substituted carboxyls showed higher fluorescence quantum yields. 41 Therefore, we decided to introduce EW bromine groups in the BINOL moiety of ( R )- 1 and ( S )- 1 to generate new chiral dyes ( R )- 2 and ( S )- 2 (Figure 1). The introduced bromines are expected to have a triple effect on the dye properties.…”

Section: Resultsmentioning

confidence: 99%

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Chiral Organic Dyes Endowed with Circularly Polarized Laser Emission

et al. 2017

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The direct generation of efficient, tunable, and switchable circularly polarized laser emission (CPLE) would have far-reaching implications in photonics and material sciences. In this paper, we describe the first chiral simple organic molecules (SOMs) capable of simultaneously sustaining significant chemical robustness, high fluorescence quantum yields, and circularly polarized luminescence (CPL) ellipticity levels (|glum|) comparable to those of similar CPL-SOMs. All these parameters altogether enable efficient laser emission and CPLE with ellipticity levels 2 orders of magnitude stronger than the intrinsic CPL ones.

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Section: Resultsmentioning

confidence: 99%

“…This result confirms, once again, the positive influence of EW groups attached to the O -moiety over the fluorescence of the O -BODIPY. 41 …”

Section: Resultsmentioning

confidence: 99%

Chiral Organic Dyes Endowed with Circularly Polarized Laser Emission

et al. 2017

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“…Replacement of the Fa toms by alkoxy,p henoxy, [31] alkynyl, [32] aryl, [33] heteroaryl, [34] Cl, [35] and carboxylatem oieties, [36] has been reported. However,t hese transformations, thoughi nteresting, lie beyondt he scope of the present paper.…”

Section: Introductionmentioning

confidence: 99%

Near‐IR BODIPY Dyes à la Carte—Programmed Orthogonal Functionalization of Rationally Designed Building Blocks

Gómez‐Durán

Esnal

Valois‐Escamilla

et al. 2015

Chemistry A European J

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Herein, we report the synthesis of polyfunctional BODIPY building blocks suitable to be subjected to several reaction sequences with complete chemoselectivity, thereby allowing the preparation of complex BODIPY derivatives in a versatile and programmable manner. The reactions included the Liebeskind-Srogl cross-coupling reaction (LSCC), nucleophilic aromatic substitution (SN Ar), Suzuki, Sonogashira, and Stille couplings, and a desulfitative reduction of the MeS group. This novel synthetic protocol is a powerful route to design a library of compounds with tailored photophysical properties for advanced applications. In this context, it is noteworthy that it offers a straightforward and cost-effective strategy to shift the BODIPY emission deep into the near-infrared spectral region while retaining high fluorescence quantum yields as well as highly efficient and stable laser action. These new dyes outperform the lasing behaviour of dyes considered as benchmarks over the red spectral region, overcoming the important drawbacks associated with these commercial laser dyes, namely low absorption at the standard pump wavelengths (355 and 532 nm) and/or poor photostability.

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“…The bathochromic shifts in the absorption and emission spectra, and the increase in the photoluminescence quantum yield of PM567 in limonene with respect to ethyl acetate, are very similar to those shown by PM567 in cyclohexane. 34 This is not surprising, since both solvents, cyclohexane and limonene, are very similar low-polar hydrocarbons.…”

Section: Resultsmentioning

confidence: 95%

Circularly polarized laser emission in optically active organic dye solutions

Cerdán

Moreno

Johnson

et al. 2017

Phys. Chem. Chem. Phys.

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The generation of circularly polarized laser emission (CPLE) in photonic devices has attracted increasing attention due to the prospects of using CP light in displaying technologies or advanced microscopies. Organic systems excel as laser materials across the whole visible spectrum, and despite many of them displaying circularly polarized luminescence (CPL), none have been shown thus far to amplify their own CPL, let alone generate CPLE. Consequently, there is still a need to find alternative CPLE organic devices. Herein we demonstrate an effective strategy for achieving strong levels of CPLE (|glum| ~ 0.1–0.2) by using solutions of an achiral dye dissolved in optically active solvents to exploit the full potential of the dynamic birefringence induced by the intense and polarized laser pumping. The present approach enables changing the CPLE handedness by changing the handedness of the solvent optical activity, opening new avenues for developing cost-effective and easily processable chiro-photonic materials.

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Carboxylates versus Fluorines: Boosting the Emission Properties of Commercial BODIPYs in Liquid and Solid Media

Abstract: Scheme 2 . Synthetic routes of derivatives 6 , 8 , and 15 from parent dye PM597. Scheme 1 . Synthetic routes of derivatives 2 , 7 , and 11 from parent dye PM567.

Cited by 62 publications

References 84 publications

Chiral Organic Dyes Endowed with Circularly Polarized Laser Emission

Chiral Organic Dyes Endowed with Circularly Polarized Laser Emission

Near‐IR BODIPY Dyes à la Carte—Programmed Orthogonal Functionalization of Rationally Designed Building Blocks

Circularly polarized laser emission in optically active organic dye solutions

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