Photoinduced charge separation via twisted intramolecular charge transfer states

Rettig, Wolfgang

doi:10.1007/3-540-57565-0_78

Cited by 209 publications

(125 citation statements)

References 114 publications

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“…A characteristic emission would be good evidence of twisted ICT states but this has been seen in only a small minority of these cases. [56][57][58] So it is not surprising that we failed to see any such evidence with our basic spectrometers.…”

Section: Resultsmentioning

confidence: 96%

Structural effects on the pH-dependent fluorescence of naphthalenic derivatives and consequences for sensing/switching

Zheng

Lynch

Rice

et al. 2012

Photochem Photobiol Sci

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Naphthalenic compounds are a rich resource for designers of fluorescent sensing/switching/logic systems. The degree of internal charge transfer (ICT) character in the fluorophore excited states can vary from negligible to substantial. 8;4,, 1,8-naphthalimides ( 16) and 4-chloro-1,8-naphthalimides (15) are of the former type. The latter type is represented by the 4-alkylamino-1,8-naphthalimides (1). Whether ICT-based or not, these serve as the fluorophore in 'fluorophore-spacerreceptor' switching systems where PET holds sway until the receptor is bound to H + . On the other hand, 4-dialkylamino-1,8-naphthalimides (3-4) show modest H + -induced fluorescence switching unless the 4-dialkylamino group is a part of a small ring (5). Electrostatic destabilization of a non-emissive twisted internal charge transfer (ICT) excited state is the origin of this behaviour. An evolution to the nonemissive twisted ICT excited state is responsible for the weak emission of the model compound 6 (and related structures 7 and 8) across the pH range. Twisted ICT excited states are also implicated in the switch 9 and its model compound 10, which are based on the 6-dialkylamino-3H-benzimidazo[2,1-a]benz [d,e]isoquinolin-3-one fluorophore. † Dedicated to Jean-Pierre Desvergne and to Hubert Le Bozec. ‡ This article is published as part of a themed issue in honour of Jean-Pierre Desvergne on the occasion of his 65th birthday.

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Section: Resultsmentioning

confidence: 96%

Structural effects on the pH-dependent fluorescence of naphthalenic derivatives and consequences for sensing/switching

Zheng

Lynch

Rice

et al. 2012

Photochem Photobiol Sci

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“…Therefore, research has been going on with a variety of new donor-acceptor charge-transfer systems and there are various models proposed to interpret the entire mechanism of photoinduced intramolecular charge transfer in DMABN and related molecular systems. [2][3][4][5][6][7] Briefly, in the twisted intramolecular charge transfer (TICT) model proposed by Grabowski et al,4 the initially generated LE state yields another minimum on the excited state potential energy surface by the twisting of the donor group into a plane perpendicular to the acceptor group, leading to a red-shifted CT emission. In the planar intramolecular charge-transfer (PICT) model, a solvent-induced vibronic coupling is supposed to take place between the LE and CT states leading to formation of a final planar structure.…”

Section: Introductionmentioning

confidence: 99%

Photoinduced intramolecular charge-transfer reactions in 4-amino-3-methyl benzoic acid methyl ester: A fluorescence study in condensed-phase and jet-cooled molecular beams

et al. 2007

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Photoinduced intramolecular charge-transfer reactions in 4-amino-3-methyl benzoic acid methyl ester (AMBME) have been investigated spectroscopically. AMBME, with its weak charge donor primary amino group, shows dual emission in polar solvents. Absorption and emission measurements in the condensed phase support the premise that the short wavelength emission band corresponds to local emission and the long wavelength emission band to the charge transfer emission. Laser-induced fluorescence excitation spectra show the presence of two low-energy conformers in jet-cooled molecular beams. Theoretical calculations using density functional theory help to determine structure, vibrational modes, potential energy surface, transition energy and oscillator strength for correlating experimental findings with theoretical results.Keywords. 4-Amino-3-methyl benzoic acid methyl ester; fluorescence; quantum yield; laser-induced fluorescence; density functional theory; supersonic jet.

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“…However, the dependence of the fluorescence emission spectra on the solvents (see Figure 2 (B)) shows that the emission spectrum of TPA-PPV becomes broad and structureless and red-shifted with the polarity increasing of solvents, which is characteristic of the twisted intramolecular charge transfer (TICT) state. [11] Such solvatochromic shifts in emission are usually associated with a drastic change of charge distribution in the excited state compared to that in the ground state. Also the linear relation between the wave numbers of the emission peaks (t f max ) and the polarity parameter E T (30) [12] of solvents (see Figure 3) provides further evidence for charge separation along the chain of TPA-PPV.…”

Section: Ground State Structuresmentioning

confidence: 99%

Photoinduced Intramolecular Charge Separation at the Repetition Units of Light-Emitting Alternating Copolymers

Yang

Lin

Zheng

et al. 2001

Macromol. Chem. Phys.

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Light‐emitting nitrogen‐containing poly‐ (phenylene vinylene) PPV‐related copolymers are synthesized by the well‐known Wittig‐Horner reaction. The alternating copolymers have hole‐transporting moieties such as triphenylamine (TPA) and conjugated aromatic units such as 1,4‐phenylene, 1,4‐ or 1,5‐naphthylene and 9,10‐anthrylene. The dipole moments within the repetition units of the copolymers in the excited state are estimated by measuring the solvent effect on absorption and fluorescence emission spectra, indicating that charge separation is present. The dipole moment values are in agreement with the electron affinities of acceptors, i. e. aromatic units. The evidence can help to elucidate the photophysical behavior, particularly the fluorescence quantum efficiencies.

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Photoinduced charge separation via twisted intramolecular charge transfer states

Cited by 209 publications

References 114 publications

Structural effects on the pH-dependent fluorescence of naphthalenic derivatives and consequences for sensing/switching

Structural effects on the pH-dependent fluorescence of naphthalenic derivatives and consequences for sensing/switching

Photoinduced intramolecular charge-transfer reactions in 4-amino-3-methyl benzoic acid methyl ester: A fluorescence study in condensed-phase and jet-cooled molecular beams

Photoinduced Intramolecular Charge Separation at the Repetition Units of Light-Emitting Alternating Copolymers

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