Photodissociation of protonated tryptamine and its supramolecular complex with 18-crown-6 ether: Dissociation times and channels, absorption spectra, and excited states calculations

Kadhane, U.; Pérot, Marie; Lucas, Bruno; Barat, M.; Fayeton, J. A.; Jouvet, Christophe; Ehlerding, Anneli; Kirketerp, M.-B.S.; Nielsen, Steen Brøndsted; Wyer, Jean Ann; Zettergren, Henning

doi:10.1016/j.cplett.2009.08.064

Cited by 14 publications

(23 citation statements)

References 27 publications

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“…Such a cage effect has already been observed in tryptamine, tryptophan, or cinchonidine itself, embedded in cyclodextrine. 53,103,104 This explains why the reactivity related to proton mobility, previously proposed for isolated CdH + , is not observed here. 53 The second role of the bisulfate is to modify the nature of the electronic transitions.…”

Section: Resultssupporting

confidence: 41%

Effects of complexation with sulfuric acid on the photodissociation of protonated Cinchona alkaloids in the gas phase

Nasr

Alata

Scuderi

et al. 2019

Phys. Chem. Chem. Phys.

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Section: Resultssupporting

confidence: 41%

Effects of complexation with sulfuric acid on the photodissociation of protonated Cinchona alkaloids in the gas phase

Nasr

Alata

Scuderi

et al. 2019

Phys. Chem. Chem. Phys.

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“…It was checked for the 4 channels that the intensity depends linearly on the photon flux, showing that photofragmentation is due to one-photon excitation. ''VV'' correlations 24 demonstrated that all the channels result from a one-step fragmentation mechanism. Thus, the m/z 94 fragment is not a secondary fragment, as suggested by the femtosecond experiment.…”

Section: Resultsmentioning

confidence: 98%

Photofragmentation in selected tautomers of protonated adenine

Cheong

Nam

Park

et al. 2011

Phys. Chem. Chem. Phys.

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The photofragmentation by UV excitation of selectively prepared 1(+) and 3(+) tautomers of protonated adenine is studied after excitation at a 266 and 263 nm wavelengths with two different experimental set-ups located in Seoul and Orsay. While the production of 1(+) tautomers with an electrospray ion source is now well accepted, calculations were used to ascribe the preparation of 3(+) tautomers from cold adenine dimers. The fragmentation patterns are rather similar for both tautomers, suggesting similar mechanisms as a statistical fragmentation in the ground electronic state after internal conversion.

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“…So, we can say in 18C6•catechol, 18C6 works like a cage to block the H atom elimination from catechol, and catechol becomes a fluorescent molecule. Notably, the similar deformation and energy rise of the 1 πσ* state by crown ether is also observed in the protonated tryptophane58 and tryptamine 59. In these cases, the electron at the photoexcited S 1 (ππ*) state is transferred to the ammonium group, generating the dissociative 1 πσ* state.…”

Section: Inclusion Complexes Of Crown Ethers With Neutral Speciesmentioning

confidence: 59%

Laser Spectroscopic Study of Cold Gas-Phase Host-Guest Complexes of Crown Ethers

Ebata

Inokuchi

2016

The Chemical Record

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The structure, molecular recognition, and inclusion effect on the photophysics of guest species are investigated for neutral and ionic cold host-guest complexes of crown ethers (CEs) in the gas phase. Here, the cold neutral host-guest complexes are produced by a supersonic expansion technique and the cold ionic complexes are generated by the combination of electrospray ionization (ESI) and a cryogenically cooled ion trap. The host species are 3n-crown-n (3nCn; n = 4, 5, 6, 8) and (di)benzo-3n-crown-n ((D)B3nCn; n = 4, 5, 6, 8). For neutral guests, we have chosen water and aromatic molecules, such as phenol and benzenediols, and as ionic species we have chosen alkali-metal ions (M(+) ). The electronic spectra and isomer-specific vibrational spectra for the complexes are observed with various laser spectroscopic methods: laser-induced fluorescence (LIF); ultraviolet-ultraviolet hole-burning (UV-UV HB); and IR-UV double resonance (IR-UV DR) spectroscopy. The obtained spectra are analyzed with the aid of quantum chemical calculations. We will discuss how the host and guest species change their flexible structures for forming best-fit stable complexes (induced fitting) and what kinds of interactions are operating for the stabilization of the complexes. For the alkali metal ion•CE complexes, we investigate the solvation effect by attaching water molecules. In addition to the ground-state stabilization problem, we will show that the complexation leads to a drastic effect on the excited-state electronic structure and dynamics of the guest species, which we call a "cage-like effect".

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Photodissociation of protonated tryptamine and its supramolecular complex with 18-crown-6 ether: Dissociation times and channels, absorption spectra, and excited states calculations

Cited by 14 publications

References 27 publications

Effects of complexation with sulfuric acid on the photodissociation of protonated Cinchona alkaloids in the gas phase

Effects of complexation with sulfuric acid on the photodissociation of protonated Cinchona alkaloids in the gas phase

Photofragmentation in selected tautomers of protonated adenine

Laser Spectroscopic Study of Cold Gas-Phase Host-Guest Complexes of Crown Ethers

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