Synthesis and absorption/emission spectroscopic properties of bis(phenylethynyl)benzenes and 9,10-bis(phenylethynyl)anthracenes

Nakatsuji, Shin’ichi; Matsuda, Kosei; Uesugi, Yukiko; Nakashima, Kenichiro; Akiyama, Shuzo; Fabian, Walter M. F.

doi:10.1039/p19920000755

Cited by 45 publications

(37 citation statements)

References 6 publications

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“…Note that similar results have already been reported for some push-pull ethynyl anthracene derivatives. [31] The fluorescence lifetimes were recorded by the singlephoton counting technique for compounds that show a high enough fluorescence quantum yield ( Table 1). Longer-lived fluorescent states were observed for anthryl derivatives.…”

Section: Absorption and Fluorescence Propertiesmentioning

confidence: 99%

Comprehensive Photophysical Behaviour of Ethynyl Fluorenes and Ethynyl Anthracenes Investigated by Fast and Ultrafast Time‐Resolved Spectroscopy

et al. 2012

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Detailed investigations by time-resolved transient absorption and fluorescence spectroscopies with nano- and femtosecond time resolutions are carried out with the aim of characterising the lowest excited singlet and triplet states of three ethynyl fluorenes (1-3) and three ethynyl anthracenes (4-6) in solvents of different polarity. The solvent is found to modify the deactivation pathways of the lowest excited singlet state of compounds 1-4, thus changing their fluorescence, intersystem crossing and internal conversion efficiencies. The fluorescence and triplet yields gradually decrease, while the internal conversion quantum yield increases upon increasing the solvent dielectric constant. These experimental results, coupled with the marked fluorosolvatochromic effect, point to the involvement of an emitting state with a charge-transfer (CT) character, strongly stabilised by polar solvents. This is proved by ultrafast spectroscopic studies in which two transients, distinguished by characteristic spectral shapes assigned to locally excited (LE) and CT states, are detected, the CT state being the longer lived and fluorescent one in highly polar solvents. The intramolecular LE→CT process, operative in highly polar media, becomes particularly fast (up to ≈300 fs) in the case of the NO(2) derivative 1. No push-pull character is found for 5 and 6, which exhibit different photophysical behaviour; indeed, the solvent polarity does not modify significantly the dynamics of the lowest excited singlet states. Quantum mechanical calculations at the TDDFT level are also used to determine the state order and nature of the lowest excited singlet and triplet states and to rationalise the different photophysical behaviour of fluorine and anthracene derivatives, particularly concerning the intersystem crossing process.

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Section: Absorption and Fluorescence Propertiesmentioning

confidence: 99%

Comprehensive Photophysical Behaviour of Ethynyl Fluorenes and Ethynyl Anthracenes Investigated by Fast and Ultrafast Time‐Resolved Spectroscopy

et al. 2012

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“…2 are shown the absorption spectra of 1 and 2 in hexane and DMF and a summary of the absorption spectroscopic data for 1 and 2 in various solvents is given in Table 1. The absorption maxima (k abs ) of 2 occur at longer wavelengths than those of 1 [4,8] and, in contrast to 1, the spectra of 2 are sensitive to solvent polarity (469 nm in hexane versus 503 nm in DMF). The bathochromic shift observed in the absorption spectra of 2 is a consequence of the presence of the nitro and amino groups at the terminii of the highly conjugated system.…”

Section: Resultsmentioning

confidence: 96%

“…2 and Table 1) might indicate that an intramolecular charge-transfer state exists in the ground state also (vide infra). Table 2 are shown the respective fluorescence spectra and data for 1 and 2 in selected solvents [4,8]. The fluorescence maxima (k em = 513 nm) of 2 in hexane occurs at a longer wavelength than that of 1 (468, 496 nm) and undergoes a solvatochromatic shift to 592 nm in chlorobenzene.…”

Section: Resultsmentioning

confidence: 98%

“…1) of the ethynylphenyl groups [14]. However, until now compounds that contain both para-acceptor and para-donor groups in the ethynylphenyl moieties have not been thoroughly studied [4,8,11,12]. In particular, the prototypical substance, 9-(4-aminophenylethynyl)-10-(4-nitrophenylethynyl)anthracene 2, has not been prepared even though it is expected to exhibit interesting linear and nonlinear optical properties.…”

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confidence: 96%

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Synthesis and Solvatochromatic properties of 9-(4-Aminophenylethynyl)-10-(4-nitrophenylethynyl)anthracene

Imoto

Takeda²,

Tamaki³

et al. 2009

Res Chem Intermed

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9-(4-Aminophenylethynyl)-10-(4-nitrophenylethynyl)anthracene (2) was synthesized in high yield by using a route involving sequential Sonogashira cross coupling reactions of 9-bromo-10-iodoanthracene with 4-nitrophenylacetylene and 4-aminophenylacetylene. Solvatochromism was observed in the absorption and fluorescence spectra of 2 in a variety of solvents. In less polar solvents, such as hexane and benzene, the fluorescence emission band of 2 appears in the green to orange region while this substance does not fluoresce in polar solvents, such as acetonitrile and DMF.

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“…These compounds were synthesized and the absorption, FL and CL spectroscopic properties were examined. 26 As shown in Fig. 8, we found a novel one-stage conversion of the CH=CH bond to the C=C bond; the compounds BPA (R=R'=NEt2 and CN; R=MeO, R'=N02) were obtained from the corresponding olefinic compounds BPB by treatment with t-BuOK in dimethylformamide (DMF) at pressure.…”

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confidence: 99%

Synthetic Analytical Studies on Organic Reagents for Biomaterials

Akiyama

1994

ANAL. SCI.

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"Synthetic analytical chemistry: Analytical chemistry with the aid of synthetic organic chemistry" is proposed by the present author as a new field of analytical chemistry. Such chemistry is developing on the basis of investigations of it-electron systems such as non-benzenoid aromatics (e.g. annulenes) or conjugated polyene and polyyne systems. Various kinds of organic reagents for analyses (ultraviolet/visible and near-infrared absorption, fluorescence, chemiluminescence and new silica gel column packings for high-performance liquid chromatography) were developed and applied to the analyses of many biomaterials. In this paper, synthetic analytical chemistry is illustrated mainly by the author's own studies.

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Synthesis and absorption/emission spectroscopic properties of bis(phenylethynyl)benzenes and 9,10-bis(phenylethynyl)anthracenes

Cited by 45 publications

References 6 publications

Comprehensive Photophysical Behaviour of Ethynyl Fluorenes and Ethynyl Anthracenes Investigated by Fast and Ultrafast Time‐Resolved Spectroscopy

Comprehensive Photophysical Behaviour of Ethynyl Fluorenes and Ethynyl Anthracenes Investigated by Fast and Ultrafast Time‐Resolved Spectroscopy

Synthesis and Solvatochromatic properties of 9-(4-Aminophenylethynyl)-10-(4-nitrophenylethynyl)anthracene

Synthetic Analytical Studies on Organic Reagents for Biomaterials

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