Intramolecular charge-transfer properties of a molecule with a large donor group: the case of 4′-(pyren-1-yl)benzonitrile

Dobkowski, Jacek; Rettig, Wolfgang; Waluk, Jacek

doi:10.1039/b204749g

Cited by 23 publications

(20 citation statements)

References 37 publications

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“…This is consistent with the higher HOMO level of TPA (~−5.34 eV) than that of the core (~−5.50 eV) together with the lower LUMO of the core (~−2.40 eV) than that of TPA (~−1.70 eV), which facilitates TPA-to-core electron transfer ( Figure 6, Table 1). ICT phenomena induced by amine-to-pyrene electron transfer were reported before [53][54][55][56]. Dual emission was also detected for 1-(p-amino-phenyl)pyrene under acidic conditions [57].…”

Section: Photophysical Propertiesmentioning

confidence: 63%

Blue Light Emitting Polyphenylene Dendrimers with Bipolar Charge Transport Moieties

et al. 2016

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Two light-emitting polyphenylene dendrimers with both hole and electron transporting moieties were synthesized and characterized. Both molecules exhibited pure blue emission solely from the pyrene core and efficient surface-to-core energy transfers when characterized in a nonpolar environment. In particular, the carbazole-and oxadiazole-functionalized dendrimer (D1) manifested a pure blue emission from the pyrene core without showing intramolecular charge transfer (ICT) in environments with increasing polarity. On the other hand, the triphenylamine-and oxadiazole-functionalized one (D2) displayed notable ICT with dual emission from both the core and an ICT state in highly polar solvents. D1, in a three-layer organic light emitting diode (OLED) by solution processing gave a pure blue emission with Commission Internationale de l'Éclairage 1931 CIE xy = (0.16, 0.12), a peak current efficiency of 0.21 cd/A and a peak luminance of 2700 cd/m 2 . This represents the first reported pure blue dendrimer emitter with bipolar charge transport and surface-to-core energy transfer in OLEDs.

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Section: Photophysical Propertiesmentioning

confidence: 63%

Blue Light Emitting Polyphenylene Dendrimers with Bipolar Charge Transport Moieties

et al. 2016

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“…In the nonpolar medium THF, the only visible transitions are those due to S 1 →S n of the Tpy, at high energy (390 nm), and those belonging to the pyrene units (in the 470-530 nm region) [54,55]. In the polar solvent (acetonitrile), the spectra present the singlet absorption of the Tpy (at 390 nm) but, at lower energy, two distinct features are present which cannot be attributed to the pyrene singlet absorption (Figure 12 bottom).…”

Section: Resultsmentioning

confidence: 99%

Metal Ion Enhanced Charge Transfer in a Terpyridine-bis-Pyrene System

D’Aléo

Cecchetto

Cola

et al. 2009

Sensors

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The synthesis, electrochemical and photophysical properties of a branched molecule 3,5-bis(pyrene-1-yl)-4′-phenyl-2,2′:6′,2″-terpyridine are reported. Spectroscopy in different solvents reveals that an optical electron transfer from the pyrene donor to the terpyridyl electron acceptor can occur in polar media, as the system displays both charge transfer (CT) absorption and CT emission. Furthermore, the study of the zinc complex as well as the bis-protonated form shows an enhancement of the electron transfer character of the system, by an increase of the acceptor strength. This is accompanied by a large increase of the non-radiative processes. With sub-nanosecond transient absorption spectroscopy, the CT state, consisting of the pyrene radical cation and the terpyridine radical anion, has been detected. At room temperature, the study of the nanosecond transient absorption spectra reveals the formation of a low-lying triplet excited state that we attribute to the pyrene moiety through which the CT state decays. At 77K, the absence of the terpyridine triplet emission also suggests the population of a low-lying triplet state of the pyrene unit.

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“…This result revealed that the stronger electron‐withdrawing substituent groups could make the phenothiazine moiety flatter. The rigid flat structure can facilitate ICT distinctly …”

Section: Resultsmentioning

confidence: 97%

Elucidating the Structure–Reactivity Correlations of Phenothiazine‐Based Fluorescent Probes toward ClO⁻

Wang

Zhang

Wang

et al. 2018

Chemistry A European J

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In this work, with the aim of developing effective molecular probes and investigating the structure-reactivity correlation, a short series of phenothiazine-based fluorescent probes are designed for the detection of ClO with differing electron push-pull groups. Sensing experiment results and single-crystal X-ray analysis with the aid of time-dependent DFT (TD-DFT) calculations reveal that substituting groups with increasing electron-withdrawing ability can increase the dihedral angle of the phenothiazine moiety and reduce the gap energy of the probes, leading to enhanced reactivity toward ClO . Both PT1 and PT2 show two-color switching upon detection of ClO . PT1, with the strong electron-donating group thiophene, shows a fluorescence color switch from salmon to blue. PT2, with a medium electron-donating/accepting group benzothiazole, shows a fluorescence color switch from red to green. However, both PT1 and PT2 show almost no response to ONOO . Through the introduction of strong electron-withdrawing ketone combined with a cyano group, PT3 shows a cyan emission upon detection of ClO and weak red emission upon detection of ONOO . HRMS and H NMR results confirm that PT1 and PT2 have the same sensing mode, in which the divalent sulfur of phenothiazine can be oxidized to sulfoxide by ClO . Upon reaction with ClO , PT3 experiences two-step reactions. It is first oxidized into the sulfone structure by ClO , and then transformed into sulfoxide phenothiazine aldehyde. Upon encountering ONOO , PT3 changes into an aldehyde structure and some nonfluorescent byproducts. Owing to their special selectivity and high sensitivity, PT1 and PT2 are applied to image the endogenous ClO in macrophage cells and zebrafish larvae. This study is expected to provide useful guidelines for probe design for various applications.

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Intramolecular charge-transfer properties of a molecule with a large donor group: the case of 4′-(pyren-1-yl)benzonitrile

Cited by 23 publications

References 37 publications

Blue Light Emitting Polyphenylene Dendrimers with Bipolar Charge Transport Moieties

Blue Light Emitting Polyphenylene Dendrimers with Bipolar Charge Transport Moieties

Metal Ion Enhanced Charge Transfer in a Terpyridine-bis-Pyrene System

Elucidating the Structure–Reactivity Correlations of Phenothiazine‐Based Fluorescent Probes toward ClO⁻

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Intramolecular charge-transfer properties of a molecule with a large donor group: the case of 4′-(pyren-1-yl)benzonitrile

Cited by 23 publications

References 37 publications

Blue Light Emitting Polyphenylene Dendrimers with Bipolar Charge Transport Moieties

Blue Light Emitting Polyphenylene Dendrimers with Bipolar Charge Transport Moieties

Metal Ion Enhanced Charge Transfer in a Terpyridine-bis-Pyrene System

Elucidating the Structure–Reactivity Correlations of Phenothiazine‐Based Fluorescent Probes toward ClO−

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Elucidating the Structure–Reactivity Correlations of Phenothiazine‐Based Fluorescent Probes toward ClO⁻