Intramolecular charge transfer in the excited state. Kinetics and configurational changes

Zachariasse, Klaas A.; Grobys, M.; Haar, Th. von der; Hebecker, A.; Il'ichev, Yu.V.; Jiang, Yun Bao; Morawski, Olaf; Kühnle, W.

doi:10.1016/s1010-6030(96)04368-7

Cited by 232 publications

(214 citation statements)

References 31 publications

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“…Similar S 1 →ICT conversions were also discovered in some small molecules [47,48]. Whether the ICT state is due to a more twisted or more planarized molecular structure than in the ground state [34,49], is not investigated here. One might anticipate, however, that the TPA moieties of D2 may undergo slight rotations with respect to the core in the ICT state due to the strong steric hindrance within the molecule (see Figure S18).…”

Section: Photophysical Propertiessupporting

confidence: 58%

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 Propertiessupporting

confidence: 58%

Blue Light Emitting Polyphenylene Dendrimers with Bipolar Charge Transport Moieties

et al. 2016

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“…32 In bare DMABN molecule, ultrafast relaxation dynamics of the S 2 charge transfer state (L alike) from the Franck-Condon geometry (planar NH 2 ) towards the TICT state (90°) has been measured in the sub picosecond regime. 33,34 In these experiments, the femtosecond pump laser (266 nm or 270 nm) brings a large excess energy, about 0.6 eV above the band origin of the S 1 (L b -like) state, which should drastically shorten the dynamics.…”

mentioning

confidence: 99%

Twisted Intramolecular Charge Transfer in Protonated Amino Pyridine

et al. 2016

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The excited state properties of protonated ortho (2-), meta (3-), and para (4-) aminopyridine molecules have been investigated through UV photofragmentation spectroscopy and excited state coupled-cluster CC2 calculations. Cryogenic ion spectroscopy allows recording well-resolved vibronic spectroscopy that can be reproduced through Franck−Condon simulations of the ππ* local minimum of the excited state potential energy surface. The excited state lifetimes have also been measured through a pump−probe excitation scheme and compared to the estimated radiative lifetimes. Although protonated aminopyridines are rather simple aromatic molecules, their deactivation mechanisms are indeed quite complex with unexpected results. In protonated 3-and 4-aminopyridine, the fragmentation yield is negligible around the band origin, which implies the absence of internal conversion to the ground state. Besides, a twisted intramolecular charge transfer reaction is evidenced in protonated 4-aminopyridine around the band origin, while excited state proton transfer from the pyridinic nitrogen to the adjacent carbon atom opens with roughly 500 cm −1 of excess energy.

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“…This phenomenon, which has been well documented in the literature, is referred to as PICT. [16] What makes the 1,2,3-triazole special comparing to other aromatic structures is the highly effective conjugation between the triazole and the N-2-aryl ring, even with the presence of theoretically free-rotatable N À C s bonds. These co-planar structures were confirmed not only by the X-ray crystal structures, as shown in earlier discussions, but also indicated by the computational studies as the most stable conformations for these molecules.…”

Section: A C H T U N G T R E N N U N G (L Max ) [Nm]mentioning

confidence: 99%

N‐2‐Aryl‐1,2,3‐triazoles: A Novel Class of UV/Blue‐Light‐Emitting Fluorophores with Tunable Optical Properties

Yan

Wang

Lin

et al. 2011

Chemistry A European J

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The N-2-aryl-1,2,3-triazole derivatives (NATs) were developed as a new class of UV/blue-light-emitting fluorophores. Though both N-1-aryl-1,2,3-triazoles and N-2-aryl-1,2,3-triazoles gave strong photo absorption under excitation at 330 nm, only the N-2-analogous showed strong fluorescence emission in the UV/blue range with high efficiency in various solvents (quantum yield Φ around 0.3-0.5). Significant substituted group effects were observed, allowing tunable optical properties with emission (λ(max)) from 350-400 nm and Stokes shift from 38-93 nm. The computational studies along with X-ray crystal structures indicated the significance of the effective conjugation between triazole ring and aryl groups on the N-2 position. The planar intramolecular charge transfer (PICT) mechanism was proposed, which was supported by solvent effect studies. Simple derivatizations gave NAT-modified lysine and strong UV/blue emitting bis-NAT (Φ=0.76, λ(max)=390), which suggested the great potential of this new class of fluorophores in biological and material science research.

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Intramolecular charge transfer in the excited state. Kinetics and configurational changes

Cited by 232 publications

References 31 publications

Blue Light Emitting Polyphenylene Dendrimers with Bipolar Charge Transport Moieties

Blue Light Emitting Polyphenylene Dendrimers with Bipolar Charge Transport Moieties

Twisted Intramolecular Charge Transfer in Protonated Amino Pyridine

N‐2‐Aryl‐1,2,3‐triazoles: A Novel Class of UV/Blue‐Light‐Emitting Fluorophores with Tunable Optical Properties

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