Dual fluorescence and intramolecular charge transfer with crystalline 4-(diisopropylamino)benzonitrile

Druzhinin, Sergey I.; Demeter, Attila; Zachariasse, Klaas A.

doi:10.1016/s0009-2614(01)01079-x

Cited by 33 publications

(58 citation statements)

References 19 publications

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“…In addition, a relatively weak red-shifted structured emission band was observed, in agreement with the spectrum of powdered DMABN crystals reported in the literature [2]. Upon lowering the temperature, the new redshifted band strongly increased in absolute and relative intensity, reaching at )110°C an intensity ratio of 23 with respect of the fluorescence band attributed to the LE state [1]. Evidence for an intramolecular charge transfer (ICT) fluorescence was not found.…”

Section: Introductionsupporting

confidence: 89%

“…The purified material was then zonerefined by using an Enraf-Nonius Rapid Zonerefiner. The crystal fluorescence spectra of this purified material were essentially the same as those obtained previously [1].…”

Section: Methodsmentioning

confidence: 77%

“…It was suggested that the shape of the additional emission band in the spectrum resembles that of DMABN phosphorescence in lowtemperature glassy media, red-shifted by around 2800 cm À1 . Such strongly red-shifted structured and quenched luminescence bands were not observed with crystals of the related aminobenzonitriles 4-(methylamino)benzonitrile (MABN) and [1].…”

Section: Introductionmentioning

confidence: 97%

“…Recently, we reported fluorescence spectra and decay curves of crystalline 4-(dimethylamino)benzonitrile (DMABN) [1]. At room temperature, the DMABN crystals mainly showed locally excited (LE) fluorescence.…”

Section: Introductionmentioning

confidence: 99%

“…The DMABN used in the experiments reported in [1] was purified by sublimation. As impurities can act as very efficient traps in crystal luminescence [3,4], a more extensive purification of DMABN was undertaken, by employing chromatography and zone refining, as described in the experimental part, in order to verify the nature of the red-shifted emission bands.…”

Section: Introductionmentioning

confidence: 99%

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Fluorescence of crystalline 4-(dimethylamino)benzonitrile. Absence of dual fluorescence and observation of single-exponential fluorescence decays

Demeter

Zachariasse

2003

Chemical Physics Letters

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The fluorescence spectrum of crystals grown from newly synthesized 4-(dimethylamino)benzonitrile (DMABN), measured from 25 down to )112°C, consists of a single emission band originating from a locally excited (LE) state. The fluorescence decay of the DMABN crystals is single exponential at all temperatures investigated. These results show that intramolecular charge transfer (ICT) does not occur in crystalline DMABN. The additional red-shifted emission bands and multiexponential fluorescence decays previously reported for DMABN crystals are attributed to a minor amount of the impurity 4-(dimethylamino)benzaldehyde, the synthetic precursor of commercial DMABN.

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Section: Introductionsupporting

confidence: 89%

Section: Methodsmentioning

confidence: 77%

Section: Introductionmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Fluorescence of crystalline 4-(dimethylamino)benzonitrile. Absence of dual fluorescence and observation of single-exponential fluorescence decays

Demeter

Zachariasse

2003

Chemical Physics Letters

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Multicolored‐Fluorescence Switching of ICT‐Type Organic Solids with Clear Color Difference: Mechanically Controlled Excited State

Zhang

Wang

Zhuang

et al. 2014

Chemistry A European J

197

106

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A donor-acceptor-type fluorophore containing a twisted diphenylacrylonitrile and triphenylamine has been developed by using the Suzuki reaction. The system indicates typical intramolecular charge-transfer properties. Upon mechanical grinding or hydrostatic pressure, the fluorophore reveals a multicolored fluorescence switching. Interestingly, a fluorescence color transition from green to red was clearly observed, and the change of photoluminescent (PL) wavelength gets close to 111 nm. The mechanisms of high-contrast mechanochromic behavior are fully investigated by techniques including powder XRD, PL lifetime, high-pressure PL lifetime, and Raman spectra analysis. The tremendous PL wavelength shift is attributed to gradual transition of excited states from the local excited state to the charge-transfer state.

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Small Nonplanar Phenothiazine-5 -oxide-Based Molecules: Structural Characterization, Photophysical, Thermal and Computational Studies

et al. 2017

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Dedicated to Professor Amit Basak on the occasion of his superannuationA series of novel non-planar phenothiazine-5-oxides (2a-l) bearing electron donating, electron withdrawing and bulky groups has been synthesized in high yields and their structural, photophysical, thermal and electronic properties are investigated and compared. All compounds are blue and blue-green emissive in solution (except 2g) and solid state respectively. Single crystal X-ray diffraction (XRD) studies of 2a, 2g, 2h, 2j and 2l indicated the effect of substituents on dihedral angles and non-planarity of the molecules; 2g and 2j with m-nitrophenyl/p-cyanophenyl as electron acceptor units exhibited "push-pull" behaviour with more planar structures, and D (donor) to A (acceptor) p-stacking interactions which was also evidenced by solvatochromic and DFT studies. Thermal gravimetric analysis (TGA) indicated good thermally stability of these compounds with thermal decomposition temperatures (T d ) in the range of 194-306 8C. Density functional theory (DFT) and time-dependent DFT approaches were employed to study the HOMO, LUMO and energy gap of these compounds.

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Dual fluorescence and intramolecular charge transfer with crystalline 4-(diisopropylamino)benzonitrile

Cited by 33 publications

References 19 publications

Fluorescence of crystalline 4-(dimethylamino)benzonitrile. Absence of dual fluorescence and observation of single-exponential fluorescence decays

Fluorescence of crystalline 4-(dimethylamino)benzonitrile. Absence of dual fluorescence and observation of single-exponential fluorescence decays

Multicolored‐Fluorescence Switching of ICT‐Type Organic Solids with Clear Color Difference: Mechanically Controlled Excited State

Small Nonplanar Phenothiazine-5 -oxide-Based Molecules: Structural Characterization, Photophysical, Thermal and Computational Studies

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