Synthesis and photophysical properties of highly fluorescent 2-aryl-6-(aryleneethynylene)-1H-indoles

Flores-Jarillo, Mariana; Álvarez‐Hernández, Alejandro; Vázquez-García, Rosa Ángeles; Arias, Eduardo; Moggio, Ivana; Torres, José Román

doi:10.1016/j.dyepig.2016.05.017

Cited by 6 publications

(2 citation statements)

References 37 publications

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“…It is wellk nown that larger PE (symmetrical) oligomers are more difficult to oxidize or reduce. [35] In general, all of these oligomers showed the reversible reduction peak of pBy with as light shift to cathodic values ( Figure 5, green),s uggesting that no significant interaction takes place between both electroactivec hromophores in the ground state.…”

Section: Electrochemical Propertiesmentioning

confidence: 81%

Dual Emission of meso‐Phenyleneethynylene–BODIPY Oligomers: Synthesis, Photophysics, and Theoretical Optoelectronic Study

Flores

León

Turlakov

et al. 2020

Chemistry A European J

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Two series of 2,5‐di(butoxy)phenyleneethynylenes, one halogenated (nPEC4‐X; n=2, 3, or 4) and the other boron‐dipyrromethene (BODIPY) terminated (nPEC4‐By; n=3, 4, or 5; By=BODIPY), were synthesized monodirectionally by the step‐by‐step approach and the molecular structure was corroborated by NMR spectroscopy (1H, 13C‐DEPTQ‐135, COSY, HSQC, HMBC, 11B, 19F) and MALDI‐TOF mass spectrometry. The multiplicity and J‐coupling constants of 1H, 11B, and 19F/11B NMR signals revealed, in the nPEC4‐By series, that the phenyl in the meso position of BODIPY becomes electronically part of the conjugation of the phenyleneethynylene chain, whereas BODIPY is electronically isolated. The photophysical, electrochemical, and theoretical studies confirm this finding because the properties of nPEC4‐By are comparable to those of the nPEC4‐X oligomers and BODIPY, indicating negligible electron communication between BODIPY and the nPEC4 moieties. Nevertheless, energy transfer (ET) from nPEC4 to BODIPY was rationalized by spectroscopy and theoretical calculations. Its yield decreases with the nPEC4 conjugation length, according to the increase in distance between the two chromophores, resulting in dual emission for the longest oligomer in which ET is quenched.

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Section: Electrochemical Propertiesmentioning

confidence: 81%

Dual Emission of meso‐Phenyleneethynylene–BODIPY Oligomers: Synthesis, Photophysics, and Theoretical Optoelectronic Study

Flores

León

Turlakov

et al. 2020

Chemistry A European J

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“…5a The compound, 2-aryl-6-(aryleneethynylene)-1H-indole derivative, displays intense uorescence with high uorescence quantum yields. 17 Considering the unique uorescent properties of benzimidazoles, indoles and their derivatives, it is envisaged that introduction of the electron donating and accepting structural moiety to an expanded p-conjugated structure could largely enhance uorescence. 18 Nevertheless, this has yet been fully understood.…”

Section: Introductionmentioning

confidence: 99%

One-pot, two-step synthesis and photophysical properties of 2-(5-phenylindol-3-yl)benzimidazole derivatives

et al. 2017

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Aggregation-induced emission with white, green, or blue luminescence from biologically-active indole derivatives

et al. 2020

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Synthesis and photophysical properties of highly fluorescent 2-aryl-6-(aryleneethynylene)-1H-indoles

Cited by 6 publications

References 37 publications

Dual Emission of meso‐Phenyleneethynylene–BODIPY Oligomers: Synthesis, Photophysics, and Theoretical Optoelectronic Study

Dual Emission of meso‐Phenyleneethynylene–BODIPY Oligomers: Synthesis, Photophysics, and Theoretical Optoelectronic Study

One-pot, two-step synthesis and photophysical properties of 2-(5-phenylindol-3-yl)benzimidazole derivatives

Aggregation-induced emission with white, green, or blue luminescence from biologically-active indole derivatives

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