Subnanosecond spectrofluorimetry of new indolocarbazole derivatives in solutions and protein complexes and their dipole moments

Nemkovich, N. A.; Kruchenok, Yu. V.; Sobchuk, A. N.; Detert, Heiner; Wrobel, Norma; Chernyavskii, E. A.

doi:10.1134/s0030400x09080189

Cited by 12 publications

(7 citation statements)

References 12 publications

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“…For synthetic strategies to carbolines, see: Spä th & Eiter (1940); Sakamoto et al (1999); Franck et al (2008). For the transition-metal-catalyzed synthesis of carbazoles, see: Letessier (2011); Nemkovich et al (2009). For the transition-metal-catalyzed synthesis of carbolines, see: , Dassonneville et al (2010).…”

Section: Related Literaturementioning

confidence: 99%

“…(2011). E67, o2341 The title compound was prepared as a part of a project focused on the transition metal catalyzed synthesis of carbazoles, see: Letessier (2011) and Nemkovich et al (2009), carbolines, see: Nissen, Schollmeyer & Detert (2011) and related indolo-annulated heterocycles, see: Dassonneville et al (2010). Whereas the β-carboline is the core of a large group of alkaloids (see: Torreiles et al (1985); Love (2006)), only a few natural δ-carbolines are known.…”

Section: Sup-1mentioning

confidence: 99%

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5-Benzyl-5H-pyrido[3,2-b]indole

2011

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The title compound, C18H14N2, was prepared by twofold Pd-catalyzed arylamination of a cyclic pyrido–benzo–iodolium salt. In the crystal, two molecules of 9-benzyl-δ-carboline form centrosymmetrical dimers with distances of 3.651 (2) Å between the centroids of the pyridine rings and 3.961 (2) Å between the centroids of the pyrrole and pyridine rings. The phenyl rings point to the other molecule in the dimer and the carboline core is essentially planar [maximum deviation of 0.027 (2) Å].

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Section: Related Literaturementioning

confidence: 99%

Section: Sup-1mentioning

confidence: 99%

5-Benzyl-5H-pyrido[3,2-b]indole

2011

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“…This is a key point for such extended molecules as oligophenylenevinylenes. The dipole moments of quadrupolar complicated organic molecules and model dendrimeric organic systems that were measured using the EOAM have been published [20][21][22][23].…”

Section: Introductionmentioning

confidence: 99%

Localized excitation effects in (E,E)-2,5-bis[2-(4-N,N-dipropylaminophenyl) ethylenyl]-3,6-dimethylpyrazine and generation of its different forms in solution

2012

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rupolar dye in 1,4-dioxane and cyclohexane in addition to its instantaneous fluorescence spectra and fluorescence lifetimes in dichloromethane (pure and with added trifluoroacetic acid) were measured. Quantumchemical calculations show that the π−π conjugated system is localized in the flattest part of the molecule due to disorder in the ground-state geometry of the dye molecule and that this part is the one responsible for light absorption. The effect of localized excitation of the dye causes a considerable change in its dipole moment Δ a μ. Various fluorescent forms of the dye that feature considerably spaced emission spectra and different fluorescence lifetimes originate by adding trifluoroacetic acid to the solution of oligophenylenevinylene in dichloromethane. Introduction.Oligophenylenevinylenes belong to a class of complicated organic compounds with an extended conjugated electron system and electron-donor and electron-acceptor groups. They are finding more and more applications in microelectronics [1-4], nonlinear optics, and biology [5][6][7][8]. They are used in microelectronics primarily in organic thin-film light-emitting diodes. Symmetric organic compounds with electron-donor and -acceptor groups in quadrupolar and octupolar positions have large transverse cross sections for two-photon absorption and are used in photodynamic therapy and other areas. These compounds are also used to generate second harmonics in nonlinear light transformers and as sensors of several biologically important cations.It was found earlier [9-14] that increasing the efficiency of donor-acceptor interactions caused the primary hyperpolarizability of complicated organic molecules to increase. Thus, efficient intramolecular charge transfer that changed significantly the dipole moment of complicated organic molecules during the transition into an electronic excited state was required in order to enhance their nonlinear optical properties. A substantial change of dipole moment of dye molecules after excitation was also important with respect to their use as fluorescent probes for studying various biological systems.The completed studies showed that the absorption and emission spectra of quadrupolar and centrosymmetric oligophenylenevinylenes underwent a significant long-wavelength shift and the Stokes shift of their fluorescence spectra increased as the solvent polarity increased [15,16]. The shape of the emission spectra of symmetric oligophenylenevinylenes typically did not change after the long-wavelength solvatochromic shift. The same was true for the long-wavelength shift of the absorption spectrum upon increasing the polarity of the organic solvent. According to the theory [17], these effects indicated that the dipole moments of the symmetric oligophenylenevinylenes changed significantly after the transition into the excited state.The electro-optical absorption method (EOAM) [18,19] (spectroscopy of the molecular Stark effect in the previous terminology [20]) enables dipole moments and polarizability of molecules in various ...

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“…As part of our interest in fluorophores with switchable optical properties and efficient two-photon absorption [12, 32, 33], we report here the synthesis of linear 2,5-distyrylpyrazines (DSP) with lateral donor groups. The pyrazine acts as an electron acceptor, resulting in a donor-acceptor-donor electronic structure of the chromophores.…”

Section: Introductionmentioning

confidence: 99%

Linear and Angular Distyrylpyrazines with Terminal Donor Groups: Synthesis, Solvatochromism, and Acidochromism of the Electronic Spectra

Schmitt

Fischer

Detert

2011

ISRN Organic Chemistry

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A series of linear and angular distyrylpyrazines and lateral donor groups has been prepared by aldol condensation between dimethylpyrazines and the appropriate aromatic aldehyde. The optical absorption and emission properties of these systems were studied in different solvents and media. The materials display a strong solvatochromism of the emission that is reflected by large red shifts of their fluorescence emission maxima on increasing the solvent polarity. This behaviour suggests a highly polar emitting state, which is characteristic of compounds that undergo an internal charge transfer upon excitation. Upon protonation, the UV-vis spectra are altered, and the fluorescence intensity of the neutral compound vanishes. These molecules can be used as colorimetric and luminescence polarity and pH sensors.

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Subnanosecond spectrofluorimetry of new indolocarbazole derivatives in solutions and protein complexes and their dipole moments

Cited by 12 publications

References 12 publications

5-Benzyl-5H-pyrido[3,2-b]indole

5-Benzyl-5H-pyrido[3,2-b]indole

Localized excitation effects in (E,E)-2,5-bis[2-(4-N,N-dipropylaminophenyl) ethylenyl]-3,6-dimethylpyrazine and generation of its different forms in solution

Linear and Angular Distyrylpyrazines with Terminal Donor Groups: Synthesis, Solvatochromism, and Acidochromism of the Electronic Spectra

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