Ultrafast deactivation mechanisms of protonated aromatic amino acids following UV excitation

Kang, Hyuk; Jouvet, Christophe; Dedonder‐Lardeux, C.; Martrenchard, S.; Grégoire, Gilles; Desfrançois, C.; Schermann, J. P.; Barat, M.; Fayeton, J. A.

doi:10.1039/b414986f

Cited by 137 publications

(189 citation statements)

References 23 publications

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“…These states involve the transfer of an electron from the π system to a σ* orbital on the protonated amine group, they are repulsive with respect to the N-H coordinate and also lower the overall stability of the, now hypervalent, NH 3 substituent. [54,55] Although direct absorption to these states typically occurs in low yield, they are known to intersect the bound π*←π states leading to rapid photodissociation. [55] Within this framework, we can expect multiple fragmentation pathways for the haloanilinium ions studied here.…”

Section: Resultsmentioning

confidence: 99%

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UV Photodissociation Action Spectroscopy of Haloanilinium Ions in a Linear Quadrupole Ion Trap Mass Spectrometer

Hansen

Kirk

Blanksby

et al. 2013

J. Am. Soc. Mass Spectrom.

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. (2013). UV photodissociation action spectroscopy of haloanilinium ions in a linear quadrupole ion trap mass spectrometer. Journal of the American Society for Mass Spectrometry, 24 (6), 932-940. UV photodissociation action spectroscopy of haloanilinium ions in a linear quadrupole ion trap mass spectrometer Abstract UV-vis photodissociation action spectroscopy is becoming increasingly prevalent because of advances in, and commercial availability of, ion trapping technologies and tunable laser sources. This study outlines in detail an instrumental arrangement, combining a commercial ion-trap mass spectrometer and tunable nanosecond pulsed laser source, for performing fully automated photodissociation action spectroscopy on gas-phase ions. The components of the instrumentation are outlined, including the optical and electronic interfacing, in addition to the control software for automating the experiment and performing online analysis of the spectra. To demonstrate the utility of this ensemble, the photodissociation action spectra of 4-chloroanilinium, 4-bromoanilinium, and 4-iodoanilinium cations are presented and discussed. Multiple photoproducts are detected in each case and the photoproduct yields are followed as a function of laser wavelength. It is shown that the wavelength-dependent partitioning of the halide loss, H loss, and NH3 loss channels can be broadly rationalized in terms of the relative carbon-halide bond dissociation energies and processes of energy redistribution. The photodissociation action spectrum of (phenyl)Ag2 + is compared with a literature spectrum as a further benchmark. AbstractUV-Vis photodissociation action spectroscopy is becoming increasingly prevalent due to advances in, and commercial availability of, ion trapping technologies and tunable laser sources. This study outlines in detail an instrumental arrangement, combining a commercial ion-trap mass spectrometer and tunable nanosecond pulsed laser source, for performing fully automated photodissociation action spectroscopy on gas-phase ions. The components of the instrumentation are outlined, including the optical and electronic interfacing, in addition to the control software for automating the experiment and performing online analysis of the spectra. To demonstrate the utility of this ensemble, the photodissociation action spectra of 4-chloroanilinium, 4-bromoanilinium and 4-iodoanilinium cations are presented and discussed. Multiple photoproducts are detected in each case and the photoproduct yields are followed as a function of laser wavelength. It is shown that the wavelength-dependent partitioning of the halide loss, H loss and NH 3 loss channels can be broadly rationalized in terms of the relative carbon-halide bond dissociation energies and processes of energy redistribution. The photodissociation action spectrum of (phenyl)Ag 2 + is compared to a literature spectrum as a further benchmark.3

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Section: Resultsmentioning

confidence: 99%

“…[54,55] Although direct absorption to these states typically occurs in low yield, they are known to intersect the bound π*←π states leading to rapid photodissociation. [55] Within this framework, we can expect multiple fragmentation pathways for the haloanilinium ions studied here.…”

Section: Resultsmentioning

confidence: 99%

UV Photodissociation Action Spectroscopy of Haloanilinium Ions in a Linear Quadrupole Ion Trap Mass Spectrometer

Hansen

Kirk

Blanksby

et al. 2013

J. Am. Soc. Mass Spectrom.

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“…[8][9][10] This is particularity true in the tryptophan case where the excited state lifetime is in the femtosecond domain for the protonated species and in the nanosecond domain for neutral tryptophan. It should be noticed that if protonation has a strong influence on the excited state lifetimes of these aromatic amino acids, the change in the excited state transition energy is very small.…”

Section: Introductionmentioning

confidence: 99%

Role of the Charge-Transfer State in the Electronic Absorption of Protonated Hydrocarbon Molecules

et al. 2010

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The vibrationally resolved electronic spectra of isolated protonated polycyclic aromatic hydrocarbons -naphthalene, anthracene, tetracene -have been recorded via neutral photofragment spectroscopy. The S 1 ←S 0 transitions are all in the visible region and do not show a monotonic red shift as a function of the molecular size as observed for the neutral analogues. Comparison with ab initio calculations indicates that this behaviour is due to the nature of the excited state, which has a pronounced charge transfer character for protonated linear PAH with an even number of aromatic rings.

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“…Electronic excitation leads to a cleavage of the C α -C β bond in the aromatic amino acid residues [48,64] ). These fragmentation channels are not abundant in CID and are thus well suited for photofragment spectroscopy.…”

Section: Uv Photofragmentation Spectramentioning

confidence: 99%

Conformation-Specific Spectroscopy of Peptide Fragment Ions in a Low-Temperature Ion Trap

Wassermann

Boyarkin

Paizs

et al. 2012

J. Am. Soc. Mass Spectrom.

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We have applied conformer-selective infrared-ultraviolet (IR-UV) double-resonance photofragment spectroscopy at low temperatures in an ion trap mass spectrometer for the spectroscopic characterization of peptide fragment ions. We investigate b-and a-type ions formed by collisioninduced dissociation from protonated leucine-enkephalin. The vibrational analysis and assignment are supported by nitrogen-15 isotopic substitution of individual amino acid residues and assisted by density functional theory calculations. Under such conditions, b-type ions of different size are found to appear exclusively as linear oxazolone structures with protonation on the Nterminus, while a rearrangement reaction is confirmed for the a 4 ion in which the side chain of the C-terminal phenylalanine residue is transferred to the N-terminal side of the molecule. The vibrational spectra that we present here provide a particularly stringent test for theoretical approaches.

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Ultrafast deactivation mechanisms of protonated aromatic amino acids following UV excitation

Cited by 137 publications

References 23 publications

UV Photodissociation Action Spectroscopy of Haloanilinium Ions in a Linear Quadrupole Ion Trap Mass Spectrometer

UV Photodissociation Action Spectroscopy of Haloanilinium Ions in a Linear Quadrupole Ion Trap Mass Spectrometer

Role of the Charge-Transfer State in the Electronic Absorption of Protonated Hydrocarbon Molecules

Conformation-Specific Spectroscopy of Peptide Fragment Ions in a Low-Temperature Ion Trap

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