Abstract

We report the first time-resolved high-harmonic spectroscopy (TR-HHS) study of a chemical bond rearrangement. We investigate the transient change of the high-harmonic signal from 1,3-cyclohexadiene (CHD), which undergoes ring-opening and isomerizes to 1,3,5-hexatriene (HT) upon photoexcitation. We associated the harmonic yield variation with the changes in the molecule’s electronic state and vibrational frequencies, which are caused by isomerization. This showed us that the electronic excited state of CHD created through two-photon absorption of 3.1 eV photons relaxes almost completely within 100 fs to the electronic ground state of CHD with vibrational excitation. Subsequently, the molecule isomerizes to HT (i.e., ring-opening occurs, around 400 fs after the excitation). The present results demonstrate that TR-HHS, which can track both electronic and nuclear dynamics, is a powerful tool for studying ultrafast photochemical reactions.

© 2018 Optical Society of America under the terms of the OSA Open Access Publishing Agreement

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2017 (3)

M. Nisoli, P. Decleva, F. Calegari, A. Palacios, and F. Martín, “Attosecond electron dynamics in molecules,” Chem. Rev. 117(16), 10760–10825 (2017).
[Crossref] [PubMed]

A. R. Attar, A. Bhattacherjee, C. D. Pemmaraju, K. Schnorr, K. D. Closser, D. Prendergast, and S. R. Leone, “Femtosecond x-ray spectroscopy of an electrocyclic ring-opening reaction,” Science 356(6333), 54–59 (2017).
[Crossref] [PubMed]

S. L. Horton, Y. Liu, P. Chakraborty, S. Matsika, and T. Weinacht, “Vibrationally assisted below-threshold ionization,” Phys. Rev. A (Coll. Park) 95(6), 063413 (2017).
[Crossref]

2016 (3)

O. Schalk, T. Geng, T. Thompson, N. Baluyot, R. D. Thomas, E. Tapavicza, and T. Hansson, “Cyclohexadiene revisited: a time-resolved photoelectron spectroscopy and ab Initio study,” J. Phys. Chem. A 120(15), 2320–2329 (2016).
[Crossref] [PubMed]

R. Iikubo, T. Sekikawa, Y. Harabuchi, and T. Taketsugu, “Structural dynamics of photochemical reactions probed by time-resolved photoelectron spectroscopy using high harmonic pulses,” Faraday Discuss. 194, 147–160 (2016).
[Crossref] [PubMed]

J. P. Marangos, “Development of high harmonic generation spectroscopy of organic molecules and biomolecules,” J. Phys. At. Mol. Opt. Phys. 49(13), 132001 (2016).
[Crossref]

2015 (6)

S. Adachi, M. Sato, and T. Suzuki, “Direct observation of ground-state product formation in a 1,3-cyclohexadiene ring-opening reaction,” J. Phys. Chem. Lett. 6(3), 343–346 (2015).
[Crossref] [PubMed]

M. P. Minitti, J. M. Budarz, A. Kirrander, J. S. Robinson, D. Ratner, T. J. Lane, D. Zhu, J. M. Glownia, M. Kozina, H. T. Lemke, M. Sikorski, Y. Feng, S. Nelson, K. Saita, B. Stankus, T. Northey, J. B. Hastings, and P. M. Weber, “Imaging molecular motion: femtosecond x-ray scattering of an electrocyclic chemical reaction,” Phys. Rev. Lett. 114(25), 255501 (2015).
[Crossref] [PubMed]

C. C. Pemberton, Y. Zhang, K. Saita, A. Kirrander, and P. M. Weber, “From the (1B) spectroscopic state to the photochemical product of the ultrafast ring-opening of 1,3-cyclohexadiene: a spectral observation of the complete reaction path,” J. Phys. Chem. A 119(33), 8832–8845 (2015).
[Crossref] [PubMed]

C. Schnedermann, M. Liebel, and P. Kukura, “Mode-specificity of vibrationally coherent internal conversion in rhodopsin during the primary visual event,” J. Am. Chem. Soc. 137(8), 2886–2891 (2015).
[Crossref] [PubMed]

R. Iikubo, T. Fujiwara, T. Sekikawa, Y. Harabuchi, S. Satoh, T. Taketsugu, and Y. Kayanuma, “Time-resolved photoelectron spectroscopy of dissociating 1,2-butadiene molecules by high harmonic pulses,” J. Phys. Chem. Lett. 6(13), 2463–2468 (2015).
[Crossref] [PubMed]

P. J. M. Johnson, A. Halpin, T. Morizumi, V. I. Prokhorenko, O. P. Ernst, and R. J. D. Miller, “Local vibrational coherences drive the primary photochemistry of vision,” Nat. Chem. 7(12), 980–986 (2015).
[Crossref] [PubMed]

2014 (2)

B. C. Arruda and R. J. Sension, “Ultrafast polyene dynamics: the ring opening of 1,3-cyclohexadiene derivatives,” Phys. Chem. Chem. Phys. 16(10), 4439–4455 (2014).
[Crossref] [PubMed]

F. Krausz and M. I. Stockman, “Attosecond metrology: from electron capture to future signal processing,” Nat. Photonics 8(3), 205–213 (2014).
[Crossref]

2013 (1)

A. Tehlar and H. J. Wörner, “Time-resolved high-harmonic spectroscopy of the photodissociation of CH3I and CF3I,” Mol. Phys. 111(14–15), 2057–2067 (2013).
[Crossref]

2012 (5)

V. S. Petrović, M. Siano, J. L. White, N. Berrah, C. Bostedt, J. D. Bozek, D. Broege, M. Chalfin, R. N. Coffee, J. Cryan, L. Fang, J. P. Farrell, L. J. Frasinski, J. M. Glownia, M. Gühr, M. Hoener, D. M. P. Holland, J. Kim, J. P. Marangos, T. Martinez, B. K. McFarland, R. S. Minns, S. Miyabe, S. Schorb, R. J. Sension, L. S. Spector, R. Squibb, H. Tao, J. G. Underwood, and P. H. Bucksbaum, “Transient X-ray fragmentation: probing a prototypical photoinduced ring opening,” Phys. Rev. Lett. 108(25), 253006 (2012).
[Crossref] [PubMed]

A. Rupenyan, J. B. Bertrand, D. M. Villeneuve, and H. J. Wörner, “All-optical measurement of high-harmonic amplitudes and phases in aligned molecules,” Phys. Rev. Lett. 108(3), 033903 (2012).
[Crossref] [PubMed]

P. M. Kraus, A. Rupenyan, and H. J. Wörner, “High-harmonic spectroscopy of oriented OCS molecules: emission of even and odd harmonics,” Phys. Rev. Lett. 109(23), 233903 (2012).
[Crossref] [PubMed]

H. Igarashi, A. Makida, M. Ito, and T. Sekikawa, “Pulse compression of phase-matched high harmonic pulses from a time-delay compensated monochromator,” Opt. Express 20(4), 3725–3732 (2012).
[Crossref] [PubMed]

J. Kim, H. Tao, J. L. White, V. S. Petrović, T. J. Martinez, and P. H. Bucksbaum, “Control of 1,3-cyclohexadiene photoisomerization using light-induced conical intersections,” J. Phys. Chem. A 116(11), 2758–2763 (2012).
[Crossref] [PubMed]

2011 (4)

C. Vozzi, M. Negro, F. Calegari, G. Sansone, M. Nisoli, S. De Silvestri, and S. Stagira, “Generalized molecular orbital tomography,” Nat. Phys. 7(10), 822–826 (2011).
[Crossref]

S. Haessler, J. Caillat, and P. Salières, “Self-probing of molecules with high harmonic generation,” J. Phys. At. Mol. Opt. Phys. 44(20), 203001 (2011).
[Crossref]

S. Deb and P. M. Weber, “The ultrafast pathway of photon-induced electrocyclic ring-opening reactions: the case of 1,3-cyclohexadiene,” Annu. Rev. Phys. Chem. 62(1), 19–39 (2011).
[Crossref] [PubMed]

H. J. Wörner, J. B. Bertrand, B. Fabre, J. Higuet, H. Ruf, A. Dubrouil, S. Patchkovskii, M. Spanner, Y. Mairesse, V. Blanchet, E. Mével, E. Constant, P. B. Corkum, and D. M. Villeneuve, “Conical intersection dynamics in NO2 probed by homodyne high-harmonic spectroscopy,” Science 334(6053), 208–212 (2011).
[Crossref] [PubMed]

2010 (4)

H. J. Wörner, J. B. Bertrand, D. V. Kartashov, P. B. Corkum, and D. M. Villeneuve, “Following a chemical reaction using high-harmonic interferometry,” Nature 466(7306), 604–607 (2010).
[Crossref] [PubMed]

S. Haessler, J. Caillat, W. Boutu, C. Giovanetti-Teixeira, T. Ruchon, T. Auguste, Z. Diveki, P. Breger, A. Maquet, B. Carré, R. Taïeb, and P. Salières, “Attosecond imaging of molecular electronic wavepackets,” Nat. Phys. 6(3), 200–206 (2010).
[Crossref]

M. Ito, Y. Kataoka, T. Okamoto, M. Yamashita, and T. Sekikawa, “Spatiotemporal characterization of single-order high harmonic pulses from time-compensated toroidal-grating monochromator,” Opt. Express 18(6), 6071–6078 (2010).
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2008 (2)

X. Zhou, R. Lock, W. Li, N. Wagner, M. M. Murnane, and H. C. Kapteyn, “Molecular recollision interferometry in high harmonic generation,” Phys. Rev. Lett. 100(7), 073902 (2008).
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2007 (2)

2006 (2)

N. L. Wagner, A. Wüest, I. P. Christov, T. Popmintchev, X. Zhou, M. M. Murnane, and H. C. Kapteyn, “Monitoring molecular dynamics using coherent electrons from high harmonic generation,” Proc. Natl. Acad. Sci. U.S.A. 103(36), 13279–13285 (2006).
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2005 (2)

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2004 (1)

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2003 (2)

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2002 (1)

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2001 (4)

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2000 (1)

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1999 (2)

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1997 (1)

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1989 (1)

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1980 (1)

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Autrey, D.

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N. C. Craig, M. C. Leyden, M. C. Moore, A. K. Patchen, T. Heuvel, T. A. Blake, T. Masiello, and R. L. Sams, “A reevaluation of the assignment of the vibrational fundamentals and the rotational analysis of bands in the high-resolution infrared spectra of trans- and cis-1,3,5-hexatriene,” J. Mol. Spectrosc. 262(1), 49–60 (2010).
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H. J. Wörner, J. B. Bertrand, B. Fabre, J. Higuet, H. Ruf, A. Dubrouil, S. Patchkovskii, M. Spanner, Y. Mairesse, V. Blanchet, E. Mével, E. Constant, P. B. Corkum, and D. M. Villeneuve, “Conical intersection dynamics in NO2 probed by homodyne high-harmonic spectroscopy,” Science 334(6053), 208–212 (2011).
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V. S. Petrović, M. Siano, J. L. White, N. Berrah, C. Bostedt, J. D. Bozek, D. Broege, M. Chalfin, R. N. Coffee, J. Cryan, L. Fang, J. P. Farrell, L. J. Frasinski, J. M. Glownia, M. Gühr, M. Hoener, D. M. P. Holland, J. Kim, J. P. Marangos, T. Martinez, B. K. McFarland, R. S. Minns, S. Miyabe, S. Schorb, R. J. Sension, L. S. Spector, R. Squibb, H. Tao, J. G. Underwood, and P. H. Bucksbaum, “Transient X-ray fragmentation: probing a prototypical photoinduced ring opening,” Phys. Rev. Lett. 108(25), 253006 (2012).
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V. S. Petrović, M. Siano, J. L. White, N. Berrah, C. Bostedt, J. D. Bozek, D. Broege, M. Chalfin, R. N. Coffee, J. Cryan, L. Fang, J. P. Farrell, L. J. Frasinski, J. M. Glownia, M. Gühr, M. Hoener, D. M. P. Holland, J. Kim, J. P. Marangos, T. Martinez, B. K. McFarland, R. S. Minns, S. Miyabe, S. Schorb, R. J. Sension, L. S. Spector, R. Squibb, H. Tao, J. G. Underwood, and P. H. Bucksbaum, “Transient X-ray fragmentation: probing a prototypical photoinduced ring opening,” Phys. Rev. Lett. 108(25), 253006 (2012).
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S. Haessler, J. Caillat, W. Boutu, C. Giovanetti-Teixeira, T. Ruchon, T. Auguste, Z. Diveki, P. Breger, A. Maquet, B. Carré, R. Taïeb, and P. Salières, “Attosecond imaging of molecular electronic wavepackets,” Nat. Phys. 6(3), 200–206 (2010).
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V. S. Petrović, M. Siano, J. L. White, N. Berrah, C. Bostedt, J. D. Bozek, D. Broege, M. Chalfin, R. N. Coffee, J. Cryan, L. Fang, J. P. Farrell, L. J. Frasinski, J. M. Glownia, M. Gühr, M. Hoener, D. M. P. Holland, J. Kim, J. P. Marangos, T. Martinez, B. K. McFarland, R. S. Minns, S. Miyabe, S. Schorb, R. J. Sension, L. S. Spector, R. Squibb, H. Tao, J. G. Underwood, and P. H. Bucksbaum, “Transient X-ray fragmentation: probing a prototypical photoinduced ring opening,” Phys. Rev. Lett. 108(25), 253006 (2012).
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Budarz, J. M.

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Calegari, F.

M. Nisoli, P. Decleva, F. Calegari, A. Palacios, and F. Martín, “Attosecond electron dynamics in molecules,” Chem. Rev. 117(16), 10760–10825 (2017).
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Carré, B.

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D. Autrey, J. Choo, and J. Laane, “Spectroscopic determination of the ring-twisting potential energy function of 1,3-cyclohexadiene and comparison with ab initio calculations,” J. Phys. Chem. A 105(45), 10230–10236 (2001).
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A. R. Attar, A. Bhattacherjee, C. D. Pemmaraju, K. Schnorr, K. D. Closser, D. Prendergast, and S. R. Leone, “Femtosecond x-ray spectroscopy of an electrocyclic ring-opening reaction,” Science 356(6333), 54–59 (2017).
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V. S. Petrović, M. Siano, J. L. White, N. Berrah, C. Bostedt, J. D. Bozek, D. Broege, M. Chalfin, R. N. Coffee, J. Cryan, L. Fang, J. P. Farrell, L. J. Frasinski, J. M. Glownia, M. Gühr, M. Hoener, D. M. P. Holland, J. Kim, J. P. Marangos, T. Martinez, B. K. McFarland, R. S. Minns, S. Miyabe, S. Schorb, R. J. Sension, L. S. Spector, R. Squibb, H. Tao, J. G. Underwood, and P. H. Bucksbaum, “Transient X-ray fragmentation: probing a prototypical photoinduced ring opening,” Phys. Rev. Lett. 108(25), 253006 (2012).
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V. S. Petrović, M. Siano, J. L. White, N. Berrah, C. Bostedt, J. D. Bozek, D. Broege, M. Chalfin, R. N. Coffee, J. Cryan, L. Fang, J. P. Farrell, L. J. Frasinski, J. M. Glownia, M. Gühr, M. Hoener, D. M. P. Holland, J. Kim, J. P. Marangos, T. Martinez, B. K. McFarland, R. S. Minns, S. Miyabe, S. Schorb, R. J. Sension, L. S. Spector, R. Squibb, H. Tao, J. G. Underwood, and P. H. Bucksbaum, “Transient X-ray fragmentation: probing a prototypical photoinduced ring opening,” Phys. Rev. Lett. 108(25), 253006 (2012).
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M. Allan, J. Dannacher, and J. P. Maier, “Radiative and fragmentation decay of the cations of trans- and cis-1,3,5-hexatriene and of all trans-1,3,5‐heptatriene in the A ̃(π−1) states, studied by emission and photoelectron–photoion coincidence spectroscopy,” J. Chem. Phys. 73(7), 3114–3122 (1980).
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X. Zhou, R. Lock, W. Li, N. Wagner, M. M. Murnane, and H. C. Kapteyn, “Molecular recollision interferometry in high harmonic generation,” Phys. Rev. Lett. 100(7), 073902 (2008).
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N. L. Wagner, A. Wüest, I. P. Christov, T. Popmintchev, X. Zhou, M. M. Murnane, and H. C. Kapteyn, “Monitoring molecular dynamics using coherent electrons from high harmonic generation,” Proc. Natl. Acad. Sci. U.S.A. 103(36), 13279–13285 (2006).
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Wandschneider, D. B.

P. Kukura, D. W. McCamant, S. Yoon, D. B. Wandschneider, and R. A. Mathies, “Structural observation of the primary isomerization in vision with femtosecond-stimulated Raman,” Science 310(5750), 1006–1009 (2005).
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Weber, P. M.

C. C. Pemberton, Y. Zhang, K. Saita, A. Kirrander, and P. M. Weber, “From the (1B) spectroscopic state to the photochemical product of the ultrafast ring-opening of 1,3-cyclohexadiene: a spectral observation of the complete reaction path,” J. Phys. Chem. A 119(33), 8832–8845 (2015).
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W. Cheng, C. L. Evans, N. Kuthirummal, and P. M. Weber, “A 9 eV superexcited state of 1,3-cyclohexadiene revealed by double resonance ionization photoelectron spectroscopy,” Chem. Phys. Lett. 349(5–6), 405–410 (2001).
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S. L. Horton, Y. Liu, P. Chakraborty, S. Matsika, and T. Weinacht, “Vibrationally assisted below-threshold ionization,” Phys. Rev. A (Coll. Park) 95(6), 063413 (2017).
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J. Kim, H. Tao, J. L. White, V. S. Petrović, T. J. Martinez, and P. H. Bucksbaum, “Control of 1,3-cyclohexadiene photoisomerization using light-induced conical intersections,” J. Phys. Chem. A 116(11), 2758–2763 (2012).
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M. W. Schmidt, K. K. Baldridge, J. A. Boatz, S. T. Elbert, M. S. Gordon, J. H. Jensen, S. Koseki, N. Matsunaga, K. A. Nguyen, S. Su, T. L. Windus, M. Dupuis, and J. A. Montgomery, “General atomic and molecular electronic structure system,” J. Comput. Chem. 14(11), 1347–1363 (1993).
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A. Tehlar and H. J. Wörner, “Time-resolved high-harmonic spectroscopy of the photodissociation of CH3I and CF3I,” Mol. Phys. 111(14–15), 2057–2067 (2013).
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N. L. Wagner, A. Wüest, I. P. Christov, T. Popmintchev, X. Zhou, M. M. Murnane, and H. C. Kapteyn, “Monitoring molecular dynamics using coherent electrons from high harmonic generation,” Proc. Natl. Acad. Sci. U.S.A. 103(36), 13279–13285 (2006).
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M. Merchán, L. Serrano-Andrés, L. S. Slater, B. O. Roos, R. McDiarmid, and X. Xing, “Electronic spectra of 1,4-cyclohexadiene and 1,3-cyclohexadiene: a combined experimental and theoretical investigation,” J. Phys. Chem. A 103(28), 5468–5476 (1999).
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H. Iikura, T. Tsuneda, T. Yanai, and K. Hirao, “A long-range correction scheme for generalized-gradient-approximation exchange functionals,” J. Chem. Phys. 115(8), 3540–3544 (2001).
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K. J. Schafer, B. Yang, L. F. DiMauro, and K. C. Kulander, “Above threshold ionization beyond the high harmonic cutoff,” Phys. Rev. Lett. 70(11), 1599–1602 (1993).
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P. Kukura, D. W. McCamant, S. Yoon, D. B. Wandschneider, and R. A. Mathies, “Structural observation of the primary isomerization in vision with femtosecond-stimulated Raman,” Science 310(5750), 1006–1009 (2005).
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J. Itatani, J. Levesque, D. Zeidler, H. Niikura, H. Pépin, J. C. Kieffer, P. B. Corkum, and D. M. Villeneuve, “Tomographic imaging of molecular orbitals,” Nature 432(7019), 867–871 (2004).
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C.-Y. Ruan, V. A. Lobastov, R. Srinivasan, B. M. Goodson, H. Ihee, and A. H. Zewail, “Ultrafast diffraction and structural dynamics: the nature of complex molecules far from equilibrium,” Proc. Natl. Acad. Sci. U.S.A. 98(13), 7117–7122 (2001).
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C. C. Pemberton, Y. Zhang, K. Saita, A. Kirrander, and P. M. Weber, “From the (1B) spectroscopic state to the photochemical product of the ultrafast ring-opening of 1,3-cyclohexadiene: a spectral observation of the complete reaction path,” J. Phys. Chem. A 119(33), 8832–8845 (2015).
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X. Zhou, R. Lock, W. Li, N. Wagner, M. M. Murnane, and H. C. Kapteyn, “Molecular recollision interferometry in high harmonic generation,” Phys. Rev. Lett. 100(7), 073902 (2008).
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S. Deb and P. M. Weber, “The ultrafast pathway of photon-induced electrocyclic ring-opening reactions: the case of 1,3-cyclohexadiene,” Annu. Rev. Phys. Chem. 62(1), 19–39 (2011).
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D. Feldman, J. W. Pike, and J. S. Adams, Vitamin D (Academic, 2011).

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Figures (10)

Fig. 1
Fig. 1 Structural formulas and corresponding three-dimensional representations of CHD and its isomers.
Fig. 2
Fig. 2 Schematic of the experimental setup. Inset shows the observed harmonic spectrum.
Fig. 3
Fig. 3 Experimentally observed yields of the 13th to 19th harmonics as a function of the pump-probe delay.
Fig. 4
Fig. 4 Interatomic distances in CHD.
Fig. 5
Fig. 5 (a) Experimentally observed yield of the 19th harmonic [identical to Fig. 3(d)]. The horizontal red lines show the average values of the data points (black dots) within the range of the length of each red line. (b) Short-time Fourier spectra of the transient harmonic yield [black dots in (a)].
Fig. 6
Fig. 6 Experimentally extracted modulation frequencies of the 19th harmonic yield (the colored curve in each panel). The curves were obtained by Fourier transforming the data points in the following delay ranges: (a) 80–400 fs, (b) 400–1000 fs, and (c) 1000–1600 fs. The black arrows depict the peak positions (in cm−1) of the spectra.
Fig. 7
Fig. 7 Simplified schematic of the TR-HHS of the randomly oriented molecular ensemble with (a) symmetric vibration and (b) asymmetric vibration. The red and blue circles depict atoms, and the arrows depict atomic displacements.
Fig. 8
Fig. 8 (a) Results of TR-HHS [identical to Figs. 3(d) and 5(a)]. (b) Results of TR-PES [replot of Fig. 4(c) in [28]]. Red points indicate the time-dependent yield of photoelectrons mainly originating from the MOs related to the C–C and CH2 bonds of CHD. Similarly, blue points show the yield of photoelectrons from the C = C bonds. (c) The result of subtracting the red points from the blue points in (b).
Fig. 9
Fig. 9 (a) Experimentally observed yield of the 13th harmonic [identical to Fig. 3(a)]. (b) Short-time Fourier spectra of the transient harmonic yield [black dots in (a)]. The results for the other harmonic orders are similarly plotted.
Fig. 10
Fig. 10 Power spectra of the modulations observed in the delay range of 80–400 fs of each harmonic order (red curves). Each red curve was obtained by Fourier transforming the data points in the delay range of 80–400 fs of Fig. 3. Similarly, yellow and blue curves were obtained from the data points in the delay ranges of 400–1000 fs and 1000–1600 fs, respectively.

Tables (3)

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Table 1 de Broglie wavelengths of the observed harmonics, assuming that the ionization energy of CHD is 8.25 eV [53].

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Table 2 Theoretically calculated and experimentally observed vibrational modes of CHD and its isomers.

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Table 3 Theoretically calculated HOMO energy levels (Calc.) and experimental values of the first ionization energies (Exp.) of CHD and its isomers.

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