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On the origin of ultrafast nonradiative transitions in nitro-polycyclic aromatic hydrocarbons: Excited-state dynamics in 1-nitronaphthalene.

The Journal of chemical physics

Reichardt C, Vogt RA, Crespo-Hernández CE.
PMID: 20001068
J Chem Phys. 2009 Dec 14;131(22):224518. doi: 10.1063/1.3272536.

The electronic energy relaxation of 1-nitronaphthalene was studied in nonpolar, aprotic, and protic solvents in the time window from femtoseconds to microseconds. Excitation at 340 or 360 nm populates the Franck-Condon S(1)(pipi( *)) state, which is proposed to bifurcate...

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Reichardt C, Vogt RA, Crespo-Hernández CE. On the origin of ultrafast nonradiative transitions in nitro-polycyclic aromatic hydrocarbons: Excited-state dynamics in 1-nitronaphthalene. J Chem Phys. 2009;131(22):224518doi: 10.1063/1.3272536.
Reichardt, C., Vogt, R. A., & Crespo-Hernández, C. E. (2009). On the origin of ultrafast nonradiative transitions in nitro-polycyclic aromatic hydrocarbons: Excited-state dynamics in 1-nitronaphthalene. The Journal of chemical physics, 131(22), 224518. https://doi.org/10.1063/1.3272536
Reichardt, Christian, et al. "On the origin of ultrafast nonradiative transitions in nitro-polycyclic aromatic hydrocarbons: Excited-state dynamics in 1-nitronaphthalene." The Journal of chemical physics vol. 131,22 (2009): 224518. doi: https://doi.org/10.1063/1.3272536
Reichardt C, Vogt RA, Crespo-Hernández CE. On the origin of ultrafast nonradiative transitions in nitro-polycyclic aromatic hydrocarbons: Excited-state dynamics in 1-nitronaphthalene. J Chem Phys. 2009 Dec 14;131(22):224518. doi: 10.1063/1.3272536. PMID: 20001068.
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Excited-state dynamics in nitro-naphthalene derivatives: intersystem crossing to the triplet manifold in hundreds of femtoseconds.

The journal of physical chemistry. A

Vogt RA, Reichardt C, Crespo-Hernández CE.
PMID: 23845162
J Phys Chem A. 2013 Aug 01;117(30):6580-8. doi: 10.1021/jp405656n. Epub 2013 Jul 11.

Femtosecond transient absorption experiments and density functional calculations are presented for 2-methyl-1-nitronaphthalene, 2-nitronaphthalene, and 1-nitronaphthalene in cyclohexane and acetonitrile solutions. Excitation of 2-methyl-1-nitronaphthalene at 340 nm populates the Franck-Condon singlet state, which bifurcates into two barrierless decay channels with...

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Vogt RA, Reichardt C, Crespo-Hernández CE. Excited-state dynamics in nitro-naphthalene derivatives: intersystem crossing to the triplet manifold in hundreds of femtoseconds. J Phys Chem A. 2013;117(30):6580-8doi: 10.1021/jp405656n.
Vogt, R. A., Reichardt, C., & Crespo-Hernández, C. E. (2013). Excited-state dynamics in nitro-naphthalene derivatives: intersystem crossing to the triplet manifold in hundreds of femtoseconds. The journal of physical chemistry. A, 117(30), 6580-8. https://doi.org/10.1021/jp405656n
Vogt, R Aaron, et al. "Excited-state dynamics in nitro-naphthalene derivatives: intersystem crossing to the triplet manifold in hundreds of femtoseconds." The journal of physical chemistry. A vol. 117,30 (2013): 6580-8. doi: https://doi.org/10.1021/jp405656n
Vogt RA, Reichardt C, Crespo-Hernández CE. Excited-state dynamics in nitro-naphthalene derivatives: intersystem crossing to the triplet manifold in hundreds of femtoseconds. J Phys Chem A. 2013 Aug 01;117(30):6580-8. doi: 10.1021/jp405656n. Epub 2013 Jul 11. PMID: 23845162.
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Separation of a Racemic Mixture of Two-Dimensional Molecular Clusters by Scanning Tunneling Microscopy.

Angewandte Chemie (International ed. in English)

Böhringer M, Morgenstern K, Schneider WD, Berndt R.
PMID: 29711806
Angew Chem Int Ed Engl. 1999 Mar 15;38(6):821-823. doi: 10.1002/(SICI)1521-3773(19990315)38:6<821::AID-ANIE821>3.0.CO;2-A.

Adsorption of sub-monolayer amounts of 1-nitronaphthalene (NN) onto Au(111) leads to the aggregation of NN decamers, which exhibit two-dimensional chirality and represent a racemic mixture. In analogy to Pasteur's experiment of 1848 a scanning tunneling microscope can be used...

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Böhringer M, Morgenstern K, Schneider WD, et al. Separation of a Racemic Mixture of Two-Dimensional Molecular Clusters by Scanning Tunneling Microscopy. Angew Chem Int Ed Engl. 1999;38(6):821-823doi: 10.1002/(SICI)1521-3773(19990315)38:6<821::AID-ANIE821>3.0.CO;2-A.
Böhringer, M., Morgenstern, K., Schneider, W. D., & Berndt, R. (1999). Separation of a Racemic Mixture of Two-Dimensional Molecular Clusters by Scanning Tunneling Microscopy. Angewandte Chemie (International ed. in English), 38(6), 821-823. https://doi.org/10.1002/(SICI)1521-3773(19990315)38:6<821::AID-ANIE821>3.0.CO;2-A
Böhringer, Matthias, et al. "Separation of a Racemic Mixture of Two-Dimensional Molecular Clusters by Scanning Tunneling Microscopy." Angewandte Chemie (International ed. in English) vol. 38,6 (1999): 821-823. doi: https://doi.org/10.1002/(SICI)1521-3773(19990315)38:6<821::AID-ANIE821>3.0.CO;2-A
Böhringer M, Morgenstern K, Schneider WD, Berndt R. Separation of a Racemic Mixture of Two-Dimensional Molecular Clusters by Scanning Tunneling Microscopy. Angew Chem Int Ed Engl. 1999 Mar 15;38(6):821-823. doi: 10.1002/(SICI)1521-3773(19990315)38:6<821::AID-ANIE821>3.0.CO;2-A. PMID: 29711806.
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Conformational control in the population of the triplet state and photoreactivity of nitronaphthalene derivatives.

The journal of physical chemistry. A

Vogt RA, Crespo-Hernández CE.
PMID: 24283295
J Phys Chem A. 2013 Dec 27;117(51):14100-8. doi: 10.1021/jp4101587. Epub 2013 Dec 05.

Nitronaphthalene derivatives (NNDs) are among the most abundant volatile nitro-polycyclic aromatic hydrocarbons found in the Earth's atmosphere. Investigations of the atmospheric degradation processes show that photolysis is the major degradation pathway under ambient conditions. In this contribution, we present...

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Vogt RA, Crespo-Hernández CE. Conformational control in the population of the triplet state and photoreactivity of nitronaphthalene derivatives. J Phys Chem A. 2013;117(51):14100-8doi: 10.1021/jp4101587.
Vogt, R. A., & Crespo-Hernández, C. E. (2013). Conformational control in the population of the triplet state and photoreactivity of nitronaphthalene derivatives. The journal of physical chemistry. A, 117(51), 14100-8. https://doi.org/10.1021/jp4101587
Vogt, R A, and Crespo-Hernández, Carlos E. "Conformational control in the population of the triplet state and photoreactivity of nitronaphthalene derivatives." The journal of physical chemistry. A vol. 117,51 (2013): 14100-8. doi: https://doi.org/10.1021/jp4101587
Vogt RA, Crespo-Hernández CE. Conformational control in the population of the triplet state and photoreactivity of nitronaphthalene derivatives. J Phys Chem A. 2013 Dec 27;117(51):14100-8. doi: 10.1021/jp4101587. Epub 2013 Dec 05. PMID: 24283295.
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Toward the Understanding of the Photophysics and Photochemistry of 1-Nitronaphthalene under Solar Radiation: The First Theoretical Evidence of a Photodegradation Intramolecular Rearrangement Mechanism Involving the Triplet States.

Journal of chemical theory and computation

Giussani A.
PMID: 26588542
J Chem Theory Comput. 2014 Sep 09;10(9):3987-95. doi: 10.1021/ct500395f.

1-Nitronaphthalene belongs to the class of nitrated polycyclic aromatic hydrocarbons, and constitutes an atmospheric pollutant commonly found in urban environments due to its production during incomplete combustions. On the basis of CASPT2//CASSCF quantum chemical calculations, the photophysics and photochemistry...

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Giussani A. Toward the Understanding of the Photophysics and Photochemistry of 1-Nitronaphthalene under Solar Radiation: The First Theoretical Evidence of a Photodegradation Intramolecular Rearrangement Mechanism Involving the Triplet States. J Chem Theory Comput. 2014;10(9):3987-95doi: 10.1021/ct500395f.
Giussani, A. (2014). Toward the Understanding of the Photophysics and Photochemistry of 1-Nitronaphthalene under Solar Radiation: The First Theoretical Evidence of a Photodegradation Intramolecular Rearrangement Mechanism Involving the Triplet States. Journal of chemical theory and computation, 10(9), 3987-95. https://doi.org/10.1021/ct500395f
Giussani, Angelo. "Toward the Understanding of the Photophysics and Photochemistry of 1-Nitronaphthalene under Solar Radiation: The First Theoretical Evidence of a Photodegradation Intramolecular Rearrangement Mechanism Involving the Triplet States." Journal of chemical theory and computation vol. 10,9 (2014): 3987-95. doi: https://doi.org/10.1021/ct500395f
Giussani A. Toward the Understanding of the Photophysics and Photochemistry of 1-Nitronaphthalene under Solar Radiation: The First Theoretical Evidence of a Photodegradation Intramolecular Rearrangement Mechanism Involving the Triplet States. J Chem Theory Comput. 2014 Sep 09;10(9):3987-95. doi: 10.1021/ct500395f. PMID: 26588542.
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Making Nitronaphthalene Fluoresce.

The journal of physical chemistry letters

Rybicka-Jasińska K, Espinoza EM, Clark JA, Derr JB, Carlos G, Morales M, Billones MK, O'Mari O, Ågren H, Baryshnikov GV, Vullev VI.
PMID: 34653339
J Phys Chem Lett. 2021 Oct 28;12(42):10295-10303. doi: 10.1021/acs.jpclett.1c02155. Epub 2021 Oct 15.

Nitroaromatic compounds are inherently nonfluorescent, and the subpicosecond lifetimes of the singlet excited states of many small nitrated polycyclic aromatic hydrocarbons, such as nitronaphthalenes, render them unfeasible for photosensitizers and photo-oxidants, despite their immensely beneficial reduction potentials. This article...

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Rybicka-Jasińska K, Espinoza EM, Clark JA, et al. Making Nitronaphthalene Fluoresce. J Phys Chem Lett. 2021;12(42):10295-10303doi: 10.1021/acs.jpclett.1c02155.
Rybicka-Jasińska, K., Espinoza, E. M., Clark, J. A., Derr, J. B., Carlos, G., Morales, M., Billones, M. K., O'Mari, O., Ågren, H., Baryshnikov, G. V., & Vullev, V. I. (2021). Making Nitronaphthalene Fluoresce. The journal of physical chemistry letters, 12(42), 10295-10303. https://doi.org/10.1021/acs.jpclett.1c02155
Rybicka-Jasińska, Katarzyna, et al. "Making Nitronaphthalene Fluoresce." The journal of physical chemistry letters vol. 12,42 (2021): 10295-10303. doi: https://doi.org/10.1021/acs.jpclett.1c02155
Rybicka-Jasińska K, Espinoza EM, Clark JA, Derr JB, Carlos G, Morales M, Billones MK, O'Mari O, Ågren H, Baryshnikov GV, Vullev VI. Making Nitronaphthalene Fluoresce. J Phys Chem Lett. 2021 Oct 28;12(42):10295-10303. doi: 10.1021/acs.jpclett.1c02155. Epub 2021 Oct 15. PMID: 34653339.
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Making Nitronaphthalene Fluoresce.

The journal of physical chemistry letters

Rybicka-Jasińska K, Espinoza EM, Clark JA, Derr JB, Carlos G, Morales M, Billones MK, O'Mari O, Ågren H, Baryshnikov GV, Vullev VI.
PMID: 34653339
J Phys Chem Lett. 2021 Oct 28;12(42):10295-10303. doi: 10.1021/acs.jpclett.1c02155. Epub 2021 Oct 15.

Nitroaromatic compounds are inherently nonfluorescent, and the subpicosecond lifetimes of the singlet excited states of many small nitrated polycyclic aromatic hydrocarbons, such as nitronaphthalenes, render them unfeasible for photosensitizers and photo-oxidants, despite their immensely beneficial reduction potentials. This article...

Cite
Rybicka-Jasińska K, Espinoza EM, Clark JA, et al. Making Nitronaphthalene Fluoresce. J Phys Chem Lett. 2021;12(42):10295-10303doi: 10.1021/acs.jpclett.1c02155.
Rybicka-Jasińska, K., Espinoza, E. M., Clark, J. A., Derr, J. B., Carlos, G., Morales, M., Billones, M. K., O'Mari, O., Ågren, H., Baryshnikov, G. V., & Vullev, V. I. (2021). Making Nitronaphthalene Fluoresce. The journal of physical chemistry letters, 12(42), 10295-10303. https://doi.org/10.1021/acs.jpclett.1c02155
Rybicka-Jasińska, Katarzyna, et al. "Making Nitronaphthalene Fluoresce." The journal of physical chemistry letters vol. 12,42 (2021): 10295-10303. doi: https://doi.org/10.1021/acs.jpclett.1c02155
Rybicka-Jasińska K, Espinoza EM, Clark JA, Derr JB, Carlos G, Morales M, Billones MK, O'Mari O, Ågren H, Baryshnikov GV, Vullev VI. Making Nitronaphthalene Fluoresce. J Phys Chem Lett. 2021 Oct 28;12(42):10295-10303. doi: 10.1021/acs.jpclett.1c02155. Epub 2021 Oct 15. PMID: 34653339.
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Nitration of moderately deactivated arenes with nitrogen dioxide and molecular oxygen under neutral conditions. Zeolite-induced enhancement of regioselectivity and reversal of isomer ratios.

Organic & biomolecular chemistry

Peng X, Fukui N, Mizuta M, Suzuki H.
PMID: 12945705
Org Biomol Chem. 2003 Jul 07;1(13):2326-35. doi: 10.1039/b301847d.

In the presence of zeolites, moderately deactivated arenes such as 1-nitronaphthalene, naphthonitriles, and methylated benzonitriles can be smoothly nitrated at room temperature by the combined action of nitrogen dioxide and molecular oxygen. The regioselectivity is considerably improved as compared...

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Peng X, Fukui N, Mizuta M, et al. Nitration of moderately deactivated arenes with nitrogen dioxide and molecular oxygen under neutral conditions. Zeolite-induced enhancement of regioselectivity and reversal of isomer ratios. Org Biomol Chem. 2003;1(13):2326-35doi: 10.1039/b301847d.
Peng, X., Fukui, N., Mizuta, M., & Suzuki, H. (2003). Nitration of moderately deactivated arenes with nitrogen dioxide and molecular oxygen under neutral conditions. Zeolite-induced enhancement of regioselectivity and reversal of isomer ratios. Organic & biomolecular chemistry, 1(13), 2326-35. https://doi.org/10.1039/b301847d
Peng, Xinhua, et al. "Nitration of moderately deactivated arenes with nitrogen dioxide and molecular oxygen under neutral conditions. Zeolite-induced enhancement of regioselectivity and reversal of isomer ratios." Organic & biomolecular chemistry vol. 1,13 (2003): 2326-35. doi: https://doi.org/10.1039/b301847d
Peng X, Fukui N, Mizuta M, Suzuki H. Nitration of moderately deactivated arenes with nitrogen dioxide and molecular oxygen under neutral conditions. Zeolite-induced enhancement of regioselectivity and reversal of isomer ratios. Org Biomol Chem. 2003 Jul 07;1(13):2326-35. doi: 10.1039/b301847d. PMID: 12945705.
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Ultrafast intersystem crossing in 1-nitronaphthalene. An experimental and computational study.

The journal of physical chemistry. A

Zugazagoitia JS, Almora-Díaz CX, Peon J.
PMID: 18166024
J Phys Chem A. 2008 Jan 24;112(3):358-65. doi: 10.1021/jp074809a. Epub 2008 Jan 01.

Previous studies have established that the major pathway for the first singlet excited state of 1-nitronaphthalene is intersystem crossing to the triplet manifold. In this contribution we present determinations of the decay of the S1 state of this compound...

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Zugazagoitia JS, Almora-Díaz CX, Peon J. Ultrafast intersystem crossing in 1-nitronaphthalene. An experimental and computational study. J Phys Chem A. 2008;112(3):358-65doi: 10.1021/jp074809a.
Zugazagoitia, J. S., Almora-Díaz, C. X., & Peon, J. (2008). Ultrafast intersystem crossing in 1-nitronaphthalene. An experimental and computational study. The journal of physical chemistry. A, 112(3), 358-65. https://doi.org/10.1021/jp074809a
Zugazagoitia, Jimena S, et al. "Ultrafast intersystem crossing in 1-nitronaphthalene. An experimental and computational study." The journal of physical chemistry. A vol. 112,3 (2008): 358-65. doi: https://doi.org/10.1021/jp074809a
Zugazagoitia JS, Almora-Díaz CX, Peon J. Ultrafast intersystem crossing in 1-nitronaphthalene. An experimental and computational study. J Phys Chem A. 2008 Jan 24;112(3):358-65. doi: 10.1021/jp074809a. Epub 2008 Jan 01. PMID: 18166024.
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Synthesis of isomeric angularly annealed dinaphthoporphyrin systems: examination of the relative positioning and orientation of ring fusion as factors influencing the porphyrin chromophore.

The Journal of organic chemistry

Manley JM, Roper TJ, Lash TD.
PMID: 15675845
J Org Chem. 2005 Feb 04;70(3):874-91. doi: 10.1021/jo040269r.

Porphyrins built up from two naphtho[1,2-c]pyrrole subunits and two beta-substituted pyrroles can produce five isomeric dinaphthoporphyrin systems. To gain insights into the effects of ring fusion on extended porphyrin chromophores, all five of these systems were synthesized in isomerically...

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Manley JM, Roper TJ, Lash TD. Synthesis of isomeric angularly annealed dinaphthoporphyrin systems: examination of the relative positioning and orientation of ring fusion as factors influencing the porphyrin chromophore. J Org Chem. 2005;70(3):874-91doi: 10.1021/jo040269r.
Manley, J. M., Roper, T. J., & Lash, T. D. (2005). Synthesis of isomeric angularly annealed dinaphthoporphyrin systems: examination of the relative positioning and orientation of ring fusion as factors influencing the porphyrin chromophore. The Journal of organic chemistry, 70(3), 874-91. https://doi.org/10.1021/jo040269r
Manley, Jerad M, et al. "Synthesis of isomeric angularly annealed dinaphthoporphyrin systems: examination of the relative positioning and orientation of ring fusion as factors influencing the porphyrin chromophore." The Journal of organic chemistry vol. 70,3 (2005): 874-91. doi: https://doi.org/10.1021/jo040269r
Manley JM, Roper TJ, Lash TD. Synthesis of isomeric angularly annealed dinaphthoporphyrin systems: examination of the relative positioning and orientation of ring fusion as factors influencing the porphyrin chromophore. J Org Chem. 2005 Feb 04;70(3):874-91. doi: 10.1021/jo040269r. PMID: 15675845.
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Singlet excited-state dynamics of nitropolycyclic aromatic hydrocarbons: direct measurements by femtosecond fluorescence up-conversion.

The journal of physical chemistry. A

Morales-Cueto R, Esquivelzeta-Rabell M, Saucedo-Zugazagoitia J, Peon J.
PMID: 17249742
J Phys Chem A. 2007 Feb 01;111(4):552-7. doi: 10.1021/jp065364d.

Understanding the dynamics of the electronically excited states of nitrated polycyclic aromatic hydrocarbons (NPAHs) is of great importance since photochemical reactions determine the atmospheric stability of these toxic pollutants. From previous studies, it is known that electronically excited NPAHs...

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Morales-Cueto R, Esquivelzeta-Rabell M, Saucedo-Zugazagoitia J, et al. Singlet excited-state dynamics of nitropolycyclic aromatic hydrocarbons: direct measurements by femtosecond fluorescence up-conversion. J Phys Chem A. 2007;111(4):552-7doi: 10.1021/jp065364d.
Morales-Cueto, R., Esquivelzeta-Rabell, M., Saucedo-Zugazagoitia, J., & Peon, J. (2007). Singlet excited-state dynamics of nitropolycyclic aromatic hydrocarbons: direct measurements by femtosecond fluorescence up-conversion. The journal of physical chemistry. A, 111(4), 552-7. https://doi.org/10.1021/jp065364d
Morales-Cueto, Rodrigo, et al. "Singlet excited-state dynamics of nitropolycyclic aromatic hydrocarbons: direct measurements by femtosecond fluorescence up-conversion." The journal of physical chemistry. A vol. 111,4 (2007): 552-7. doi: https://doi.org/10.1021/jp065364d
Morales-Cueto R, Esquivelzeta-Rabell M, Saucedo-Zugazagoitia J, Peon J. Singlet excited-state dynamics of nitropolycyclic aromatic hydrocarbons: direct measurements by femtosecond fluorescence up-conversion. J Phys Chem A. 2007 Feb 01;111(4):552-7. doi: 10.1021/jp065364d. PMID: 17249742.
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Bioassay of 1-nitronaphthalene for possible carcinogenicity.

National Cancer Institute carcinogenesis technical report series

[No authors listed]
PMID: 12830233
Natl Cancer Inst Carcinog Tech Rep Ser. 1978;64:1-118.

A bioassay of technical-grade 1-nitronaphthalene for possible carcinogenicity was conducted using Fischer 344 rats and B6C3F1 mice. 1-Nitronaphthalene was administered in the feed, at either of two concentrations, to groups of 50 male and 50 female animals of each...

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Bioassay of 1-nitronaphthalene for possible carcinogenicity. Natl Cancer Inst Carcinog Tech Rep Ser. 1978;64:1-118
(1978). Bioassay of 1-nitronaphthalene for possible carcinogenicity. National Cancer Institute carcinogenesis technical report series, 641-118.
"Bioassay of 1-nitronaphthalene for possible carcinogenicity." National Cancer Institute carcinogenesis technical report series vol. 64 (1978): 1-118.
Bioassay of 1-nitronaphthalene for possible carcinogenicity. Natl Cancer Inst Carcinog Tech Rep Ser. 1978;64:1-118. PMID: 12830233.
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Showing 1 to 12 of 23 entries