Gas-phase reactivities and interchromophoric effects in 1,n-dicarbazolylalkane cations and related species

Schildcrout, Steven M.; Krafcik, Randolph B.; Masnovi, John

doi:10.1021/jo00025a015

Cited by 6 publications

(11 citation statements)

References 10 publications

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“…These two likely form M 2+ as well, but identification and quantitation are problematic against intense interfering signals from [(1/2)M] + at m / z 191 and 205, respectively. Where they can be quantified, the relative abundances of M 2+ are about 5%, comparable to about 3% for the dicarbazolylalkane analogs 25…”

Section: Resultsmentioning

confidence: 93%

“…That neither is strongly dependent on CID energy supports the formulation that they are competitive, not serial, processes. Neither process is significant in EI of the analogous dicarbazolylalkanes 25…”

Section: Resultsmentioning

confidence: 98%

“…CID spectra were obtained as previously described42 using rf peak excitation potentials of 600 and 700 mV. Data processing, verification of the origin of ions, verification of their chemical assignments and corrections for natural‐isotopic peaks were carried out as previously described 25. In order to better compare the spectra of these related compounds, relative monoisotopic ion abundances from EI are reported as percent of the total ion abundance rather than as percent of the abundance of the base peak.…”

Section: Methodsmentioning

confidence: 99%

“…The mechanism for charge transport in such polymers involves ‘hole hopping,’ in which a cationic carbazolyl group captures an electron from a neighboring uncharged carbazolyl moiety in the polymer by migration of the electron through the intervening space 7–11. These conducting organic polymers have been used in many applications, including in optoelectronics and imaging, nonlinear optical materials and diodes12–24 We have used dicarbazolylalkanes, which contain two pendent carbazolyl groups, to model the interactions in such conducting polymers 25. Simplification of the interactions to pairs of aryl groups facilitates the determination of the properties and interrelations of these groups by focusing on the dynamics associated with a single electron‐transfer process.…”

Section: Introductionmentioning

confidence: 99%

“…The dominant fragmentation process for each of n = 1–5 is α‐cleavage (Scheme ), with an apparent competing McLafferty rearrangement for n = 3 only. The latter gives an ion with 6% of the abundance of the ion from the α‐cleavage 25…”

Section: Introductionmentioning

confidence: 99%

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Gaseous cation chemistry and chain‐length effects in electron ionization and collision‐induced dissociation mass spectraof symmetric 1,n‐bis(9‐anthracenyl)alkanes

Schildcrout

Masnovi

2011

J. Mass Spectrom.

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The behavior of the gaseous cations resulting from EI (30 and 70 eV) of the bichromophoric title compounds 1-5 (for n = 1-5, respectively) is examined by ion-trap mass spectrometry, including collision-induced dissociation (CID) with variation in collision energy. These results are compared with those from anthracene and 9-methylanthracene and with previously reported mass spectrometric results for 3 and dicarbazolylalkanes. Rather than using the kinetic method to obtain ion energetics where the fragmentation mechanism is clear, as commonly done, the method is used here with relative complementary-ion abundances from CID to test the proposed fragmentation mechanisms using B3LYP calculations of relative ionization energies and optimized geometries of ionic and neutral fragments. Hydrogen migrations are common, and skeletal rearrangements including formation of expanded, fused and spiro rings are proposed in several cases. Of the chain cleavages, α-homolysis giving C(15) H(11) (+) , likely as dibenzotropylium, is most important for each of 1-5 except 3, where β-cleavage to C(16) H(13) (+) dominates with a proposed methyldibenzotropylium structure. α-Cleavage was important also in the dicarbazolylalkanes. A previous inference of a McLafferty rearrangement to explain C(15) H(12) (+•) from 3 is not supported by the present results. The fragmentation behavior of 1-5 depends strongly on n and implies significant interchromophoric interaction between anthracenyl groups.

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Section: Resultsmentioning

confidence: 93%

Section: Resultsmentioning

confidence: 98%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Gaseous cation chemistry and chain‐length effects in electron ionization and collision‐induced dissociation mass spectraof symmetric 1,n‐bis(9‐anthracenyl)alkanes

Schildcrout

Masnovi

2011

J. Mass Spectrom.

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An Efficient Ultrasound‐Assisted Synthesis of N‐Alkyl Derivatives of Carbazole, Indole, and Phenothiazine

Zhao

Kang

et al. 2013

Journal of Heterocyclic Chem

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Heterocyclic compounds bearing an acidic hydrogen atom attached to nitrogen such as carbazole, indole, and phenothiazine can be efficiently alkylated in DMSO or N,N‐DMF under ultrasonic irradiation in the presence of potassium hydroxide as a base. In almost all cases, a dramatic reduction of the reaction time results and a clear yield increase accompanied by an improved quality of the products occurs.

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Microwave-assisted synthesis of amorphous cobalt nanoparticle decorated N-doped biochar for highly efficient degradation of sulfamethazine via peroxymonosulfate activation

Zhao

Zhang

et al. 2022

Journal of Water Process Engineering

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Gas-phase reactivities and interchromophoric effects in 1,n-dicarbazolylalkane cations and related species

Cited by 6 publications

References 10 publications

Gaseous cation chemistry and chain‐length effects in electron ionization and collision‐induced dissociation mass spectraof symmetric 1,n‐bis(9‐anthracenyl)alkanes

Gaseous cation chemistry and chain‐length effects in electron ionization and collision‐induced dissociation mass spectraof symmetric 1,n‐bis(9‐anthracenyl)alkanes

An Efficient Ultrasound‐Assisted Synthesis of N‐Alkyl Derivatives of Carbazole, Indole, and Phenothiazine

Microwave-assisted synthesis of amorphous cobalt nanoparticle decorated N-doped biochar for highly efficient degradation of sulfamethazine via peroxymonosulfate activation

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