Abstract

Herein, three-photon absorption (3PA) effect of a symmetrical fluorene-based molecule, pumped with 38 ps Q-switched 1064 nm laser pulses, is reported. An accurate Gaussian fitting method is used to obtain the three-photon absorption cross-section. The obtained three-photon absorption cross-section, 8.54×10-76 cm6 s2, is very high. The irradiance limiting nonlinear transmittance is as low as 2% when the incident irradiance is 120 GW/cm2. The geometry and electronic transition of the molecule are systematically studied by AM1 and TD SCF/DFT methods.

© 2008 Optical Society of America

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  1. S. Singh and L. T. Bradley, "Three-Photon Absorption in Naphthalene Crystals by Laser Excitation," Phys. Rev. Lett. 12, 612-614 (1964).
    [CrossRef]
  2. F. E. Hernández, K. D. Belfield, and I. Cohanoschi, "Three-photon absorption enhancement in a symmetrical charge transfer fluorene derivative," Chem. Phys. Lett. 391, 22-26 (2004).
    [CrossRef]
  3. S. Maiti, J. B. Shear, R. M. Wolliams, W. R. Zipfel, and W. W. Webb, "Measuring Serotonin Distribution in Live Cells with Three-Photon Excitation," Science 275, 530-532 (1997).
    [CrossRef] [PubMed]
  4. H. Szmacinski and I. Gryczynski, "Three-photon induced fluorescence of the calcium probe Indo-1," Biophys. J. 70, 547-555 (1996).
    [CrossRef] [PubMed]
  5. M. Gu, "Resolution in three-photon fluorescence scanning microscopy," Opt. Lett. 21, 988-910 (1996).
    [CrossRef] [PubMed]
  6. G. S. He, P. P. Markowicz, T. Lin, and P. N. Prasad, "Observation of stimulated emission by direct three-photon excitation," Nature 415, 767-770 (2002).
    [CrossRef] [PubMed]
  7. G. S. He, J. D. Bhawalkar, and P. N. Prasad, "Three-photon-absorption-induced fluorescence and optical limiting effects in an organic compound," Opt. Lett. 20, 1524-1526 (1995).
    [CrossRef] [PubMed]
  8. D. Wang, C. Zhan, Y. Chen, Y. J. Li, Z. Z. Lu, and Y. X. Nie, "Large optical power limiting induced by three-photon absorption of two stilbazolium-like dyes," Chem. Phys. Lett. 369, 621-626 (2003).
    [CrossRef]
  9. Y. Mao, J. Liu, W. Ma, Y. Wu, and Y. Cheng, "Three-photon absorption-induced fluorescence and optical limiting effects in a fluorene derivative," J. Mod. Opt. 54, 77-84 (2007).
    [CrossRef]
  10. V. Kimberg, S. Polyutov, F. Gel’mukhanov, and H. Ågren, "Dynamics of cavityless lasing generated by ultrafast multiphoton excitation," Phys. Rev. A 74, 033814 (2006).
    [CrossRef]
  11. K. D. Belfield, K. J. Schafer, W. Mourad, and B. A. Reinhardt, "Synthesis of New Two-Photon Absorbing Fluorene Derivatives via Cu-Mediated Ullmann Condensations," J. Org. Chem. 65, 4475-4481 (2000).
    [CrossRef] [PubMed]
  12. I. Cohanoschi, M. García, C. Toro, K. D. Belfield, and F. E. Hernández, "Three-photon absorption of a new series of halogenated fluorene derivatives," Chem. Phys. Lett. 430, 133-138 (2006).
    [CrossRef]
  13. I. Cohanoschi, K. D. Belfied, C. Toro, and F. E. Hernández, "Solvent effects on the three-photon absorption cross-section of a highly conjugated fluorene derivative," J. Chem. Phys. 125, 161102 (2006).
    [CrossRef] [PubMed]
  14. P. Cronstrand, Y. Luo, P. Norman, and H. Agren, "Ab initio calculations of three-photon absorption," Chem. Phys. Lett. 375, 233-239 (2003).
    [CrossRef]

2007

Y. Mao, J. Liu, W. Ma, Y. Wu, and Y. Cheng, "Three-photon absorption-induced fluorescence and optical limiting effects in a fluorene derivative," J. Mod. Opt. 54, 77-84 (2007).
[CrossRef]

2006

V. Kimberg, S. Polyutov, F. Gel’mukhanov, and H. Ågren, "Dynamics of cavityless lasing generated by ultrafast multiphoton excitation," Phys. Rev. A 74, 033814 (2006).
[CrossRef]

I. Cohanoschi, M. García, C. Toro, K. D. Belfield, and F. E. Hernández, "Three-photon absorption of a new series of halogenated fluorene derivatives," Chem. Phys. Lett. 430, 133-138 (2006).
[CrossRef]

I. Cohanoschi, K. D. Belfied, C. Toro, and F. E. Hernández, "Solvent effects on the three-photon absorption cross-section of a highly conjugated fluorene derivative," J. Chem. Phys. 125, 161102 (2006).
[CrossRef] [PubMed]

2004

F. E. Hernández, K. D. Belfield, and I. Cohanoschi, "Three-photon absorption enhancement in a symmetrical charge transfer fluorene derivative," Chem. Phys. Lett. 391, 22-26 (2004).
[CrossRef]

2003

D. Wang, C. Zhan, Y. Chen, Y. J. Li, Z. Z. Lu, and Y. X. Nie, "Large optical power limiting induced by three-photon absorption of two stilbazolium-like dyes," Chem. Phys. Lett. 369, 621-626 (2003).
[CrossRef]

P. Cronstrand, Y. Luo, P. Norman, and H. Agren, "Ab initio calculations of three-photon absorption," Chem. Phys. Lett. 375, 233-239 (2003).
[CrossRef]

2002

G. S. He, P. P. Markowicz, T. Lin, and P. N. Prasad, "Observation of stimulated emission by direct three-photon excitation," Nature 415, 767-770 (2002).
[CrossRef] [PubMed]

2000

K. D. Belfield, K. J. Schafer, W. Mourad, and B. A. Reinhardt, "Synthesis of New Two-Photon Absorbing Fluorene Derivatives via Cu-Mediated Ullmann Condensations," J. Org. Chem. 65, 4475-4481 (2000).
[CrossRef] [PubMed]

1997

S. Maiti, J. B. Shear, R. M. Wolliams, W. R. Zipfel, and W. W. Webb, "Measuring Serotonin Distribution in Live Cells with Three-Photon Excitation," Science 275, 530-532 (1997).
[CrossRef] [PubMed]

1996

H. Szmacinski and I. Gryczynski, "Three-photon induced fluorescence of the calcium probe Indo-1," Biophys. J. 70, 547-555 (1996).
[CrossRef] [PubMed]

M. Gu, "Resolution in three-photon fluorescence scanning microscopy," Opt. Lett. 21, 988-910 (1996).
[CrossRef] [PubMed]

1995

1964

S. Singh and L. T. Bradley, "Three-Photon Absorption in Naphthalene Crystals by Laser Excitation," Phys. Rev. Lett. 12, 612-614 (1964).
[CrossRef]

Agren, H.

P. Cronstrand, Y. Luo, P. Norman, and H. Agren, "Ab initio calculations of three-photon absorption," Chem. Phys. Lett. 375, 233-239 (2003).
[CrossRef]

Ågren, H.

V. Kimberg, S. Polyutov, F. Gel’mukhanov, and H. Ågren, "Dynamics of cavityless lasing generated by ultrafast multiphoton excitation," Phys. Rev. A 74, 033814 (2006).
[CrossRef]

Belfied, K. D.

I. Cohanoschi, K. D. Belfied, C. Toro, and F. E. Hernández, "Solvent effects on the three-photon absorption cross-section of a highly conjugated fluorene derivative," J. Chem. Phys. 125, 161102 (2006).
[CrossRef] [PubMed]

Belfield, K. D.

I. Cohanoschi, M. García, C. Toro, K. D. Belfield, and F. E. Hernández, "Three-photon absorption of a new series of halogenated fluorene derivatives," Chem. Phys. Lett. 430, 133-138 (2006).
[CrossRef]

F. E. Hernández, K. D. Belfield, and I. Cohanoschi, "Three-photon absorption enhancement in a symmetrical charge transfer fluorene derivative," Chem. Phys. Lett. 391, 22-26 (2004).
[CrossRef]

K. D. Belfield, K. J. Schafer, W. Mourad, and B. A. Reinhardt, "Synthesis of New Two-Photon Absorbing Fluorene Derivatives via Cu-Mediated Ullmann Condensations," J. Org. Chem. 65, 4475-4481 (2000).
[CrossRef] [PubMed]

Bhawalkar, J. D.

Bradley, L. T.

S. Singh and L. T. Bradley, "Three-Photon Absorption in Naphthalene Crystals by Laser Excitation," Phys. Rev. Lett. 12, 612-614 (1964).
[CrossRef]

Chen, Y.

D. Wang, C. Zhan, Y. Chen, Y. J. Li, Z. Z. Lu, and Y. X. Nie, "Large optical power limiting induced by three-photon absorption of two stilbazolium-like dyes," Chem. Phys. Lett. 369, 621-626 (2003).
[CrossRef]

Cheng, Y.

Y. Mao, J. Liu, W. Ma, Y. Wu, and Y. Cheng, "Three-photon absorption-induced fluorescence and optical limiting effects in a fluorene derivative," J. Mod. Opt. 54, 77-84 (2007).
[CrossRef]

Cohanoschi, I.

I. Cohanoschi, M. García, C. Toro, K. D. Belfield, and F. E. Hernández, "Three-photon absorption of a new series of halogenated fluorene derivatives," Chem. Phys. Lett. 430, 133-138 (2006).
[CrossRef]

I. Cohanoschi, K. D. Belfied, C. Toro, and F. E. Hernández, "Solvent effects on the three-photon absorption cross-section of a highly conjugated fluorene derivative," J. Chem. Phys. 125, 161102 (2006).
[CrossRef] [PubMed]

F. E. Hernández, K. D. Belfield, and I. Cohanoschi, "Three-photon absorption enhancement in a symmetrical charge transfer fluorene derivative," Chem. Phys. Lett. 391, 22-26 (2004).
[CrossRef]

Cronstrand, P.

P. Cronstrand, Y. Luo, P. Norman, and H. Agren, "Ab initio calculations of three-photon absorption," Chem. Phys. Lett. 375, 233-239 (2003).
[CrossRef]

García, M.

I. Cohanoschi, M. García, C. Toro, K. D. Belfield, and F. E. Hernández, "Three-photon absorption of a new series of halogenated fluorene derivatives," Chem. Phys. Lett. 430, 133-138 (2006).
[CrossRef]

Gel’mukhanov, F.

V. Kimberg, S. Polyutov, F. Gel’mukhanov, and H. Ågren, "Dynamics of cavityless lasing generated by ultrafast multiphoton excitation," Phys. Rev. A 74, 033814 (2006).
[CrossRef]

Gryczynski, I.

H. Szmacinski and I. Gryczynski, "Three-photon induced fluorescence of the calcium probe Indo-1," Biophys. J. 70, 547-555 (1996).
[CrossRef] [PubMed]

Gu, M.

He, G. S.

G. S. He, P. P. Markowicz, T. Lin, and P. N. Prasad, "Observation of stimulated emission by direct three-photon excitation," Nature 415, 767-770 (2002).
[CrossRef] [PubMed]

G. S. He, J. D. Bhawalkar, and P. N. Prasad, "Three-photon-absorption-induced fluorescence and optical limiting effects in an organic compound," Opt. Lett. 20, 1524-1526 (1995).
[CrossRef] [PubMed]

Hernández, F. E.

I. Cohanoschi, M. García, C. Toro, K. D. Belfield, and F. E. Hernández, "Three-photon absorption of a new series of halogenated fluorene derivatives," Chem. Phys. Lett. 430, 133-138 (2006).
[CrossRef]

I. Cohanoschi, K. D. Belfied, C. Toro, and F. E. Hernández, "Solvent effects on the three-photon absorption cross-section of a highly conjugated fluorene derivative," J. Chem. Phys. 125, 161102 (2006).
[CrossRef] [PubMed]

F. E. Hernández, K. D. Belfield, and I. Cohanoschi, "Three-photon absorption enhancement in a symmetrical charge transfer fluorene derivative," Chem. Phys. Lett. 391, 22-26 (2004).
[CrossRef]

Kimberg, V.

V. Kimberg, S. Polyutov, F. Gel’mukhanov, and H. Ågren, "Dynamics of cavityless lasing generated by ultrafast multiphoton excitation," Phys. Rev. A 74, 033814 (2006).
[CrossRef]

Li, Y. J.

D. Wang, C. Zhan, Y. Chen, Y. J. Li, Z. Z. Lu, and Y. X. Nie, "Large optical power limiting induced by three-photon absorption of two stilbazolium-like dyes," Chem. Phys. Lett. 369, 621-626 (2003).
[CrossRef]

Lin, T.

G. S. He, P. P. Markowicz, T. Lin, and P. N. Prasad, "Observation of stimulated emission by direct three-photon excitation," Nature 415, 767-770 (2002).
[CrossRef] [PubMed]

Liu, J.

Y. Mao, J. Liu, W. Ma, Y. Wu, and Y. Cheng, "Three-photon absorption-induced fluorescence and optical limiting effects in a fluorene derivative," J. Mod. Opt. 54, 77-84 (2007).
[CrossRef]

Lu, Z. Z.

D. Wang, C. Zhan, Y. Chen, Y. J. Li, Z. Z. Lu, and Y. X. Nie, "Large optical power limiting induced by three-photon absorption of two stilbazolium-like dyes," Chem. Phys. Lett. 369, 621-626 (2003).
[CrossRef]

Luo, Y.

P. Cronstrand, Y. Luo, P. Norman, and H. Agren, "Ab initio calculations of three-photon absorption," Chem. Phys. Lett. 375, 233-239 (2003).
[CrossRef]

Ma, W.

Y. Mao, J. Liu, W. Ma, Y. Wu, and Y. Cheng, "Three-photon absorption-induced fluorescence and optical limiting effects in a fluorene derivative," J. Mod. Opt. 54, 77-84 (2007).
[CrossRef]

Maiti, S.

S. Maiti, J. B. Shear, R. M. Wolliams, W. R. Zipfel, and W. W. Webb, "Measuring Serotonin Distribution in Live Cells with Three-Photon Excitation," Science 275, 530-532 (1997).
[CrossRef] [PubMed]

Mao, Y.

Y. Mao, J. Liu, W. Ma, Y. Wu, and Y. Cheng, "Three-photon absorption-induced fluorescence and optical limiting effects in a fluorene derivative," J. Mod. Opt. 54, 77-84 (2007).
[CrossRef]

Markowicz, P. P.

G. S. He, P. P. Markowicz, T. Lin, and P. N. Prasad, "Observation of stimulated emission by direct three-photon excitation," Nature 415, 767-770 (2002).
[CrossRef] [PubMed]

Mourad, W.

K. D. Belfield, K. J. Schafer, W. Mourad, and B. A. Reinhardt, "Synthesis of New Two-Photon Absorbing Fluorene Derivatives via Cu-Mediated Ullmann Condensations," J. Org. Chem. 65, 4475-4481 (2000).
[CrossRef] [PubMed]

Nie, Y. X.

D. Wang, C. Zhan, Y. Chen, Y. J. Li, Z. Z. Lu, and Y. X. Nie, "Large optical power limiting induced by three-photon absorption of two stilbazolium-like dyes," Chem. Phys. Lett. 369, 621-626 (2003).
[CrossRef]

Norman, P.

P. Cronstrand, Y. Luo, P. Norman, and H. Agren, "Ab initio calculations of three-photon absorption," Chem. Phys. Lett. 375, 233-239 (2003).
[CrossRef]

Polyutov, S.

V. Kimberg, S. Polyutov, F. Gel’mukhanov, and H. Ågren, "Dynamics of cavityless lasing generated by ultrafast multiphoton excitation," Phys. Rev. A 74, 033814 (2006).
[CrossRef]

Prasad, P. N.

G. S. He, P. P. Markowicz, T. Lin, and P. N. Prasad, "Observation of stimulated emission by direct three-photon excitation," Nature 415, 767-770 (2002).
[CrossRef] [PubMed]

G. S. He, J. D. Bhawalkar, and P. N. Prasad, "Three-photon-absorption-induced fluorescence and optical limiting effects in an organic compound," Opt. Lett. 20, 1524-1526 (1995).
[CrossRef] [PubMed]

Reinhardt, B. A.

K. D. Belfield, K. J. Schafer, W. Mourad, and B. A. Reinhardt, "Synthesis of New Two-Photon Absorbing Fluorene Derivatives via Cu-Mediated Ullmann Condensations," J. Org. Chem. 65, 4475-4481 (2000).
[CrossRef] [PubMed]

Schafer, K. J.

K. D. Belfield, K. J. Schafer, W. Mourad, and B. A. Reinhardt, "Synthesis of New Two-Photon Absorbing Fluorene Derivatives via Cu-Mediated Ullmann Condensations," J. Org. Chem. 65, 4475-4481 (2000).
[CrossRef] [PubMed]

Shear, J. B.

S. Maiti, J. B. Shear, R. M. Wolliams, W. R. Zipfel, and W. W. Webb, "Measuring Serotonin Distribution in Live Cells with Three-Photon Excitation," Science 275, 530-532 (1997).
[CrossRef] [PubMed]

Singh, S.

S. Singh and L. T. Bradley, "Three-Photon Absorption in Naphthalene Crystals by Laser Excitation," Phys. Rev. Lett. 12, 612-614 (1964).
[CrossRef]

Szmacinski, H.

H. Szmacinski and I. Gryczynski, "Three-photon induced fluorescence of the calcium probe Indo-1," Biophys. J. 70, 547-555 (1996).
[CrossRef] [PubMed]

Toro, C.

I. Cohanoschi, M. García, C. Toro, K. D. Belfield, and F. E. Hernández, "Three-photon absorption of a new series of halogenated fluorene derivatives," Chem. Phys. Lett. 430, 133-138 (2006).
[CrossRef]

I. Cohanoschi, K. D. Belfied, C. Toro, and F. E. Hernández, "Solvent effects on the three-photon absorption cross-section of a highly conjugated fluorene derivative," J. Chem. Phys. 125, 161102 (2006).
[CrossRef] [PubMed]

Wang, D.

D. Wang, C. Zhan, Y. Chen, Y. J. Li, Z. Z. Lu, and Y. X. Nie, "Large optical power limiting induced by three-photon absorption of two stilbazolium-like dyes," Chem. Phys. Lett. 369, 621-626 (2003).
[CrossRef]

Webb, W. W.

S. Maiti, J. B. Shear, R. M. Wolliams, W. R. Zipfel, and W. W. Webb, "Measuring Serotonin Distribution in Live Cells with Three-Photon Excitation," Science 275, 530-532 (1997).
[CrossRef] [PubMed]

Wolliams, R. M.

S. Maiti, J. B. Shear, R. M. Wolliams, W. R. Zipfel, and W. W. Webb, "Measuring Serotonin Distribution in Live Cells with Three-Photon Excitation," Science 275, 530-532 (1997).
[CrossRef] [PubMed]

Wu, Y.

Y. Mao, J. Liu, W. Ma, Y. Wu, and Y. Cheng, "Three-photon absorption-induced fluorescence and optical limiting effects in a fluorene derivative," J. Mod. Opt. 54, 77-84 (2007).
[CrossRef]

Zhan, C.

D. Wang, C. Zhan, Y. Chen, Y. J. Li, Z. Z. Lu, and Y. X. Nie, "Large optical power limiting induced by three-photon absorption of two stilbazolium-like dyes," Chem. Phys. Lett. 369, 621-626 (2003).
[CrossRef]

Zipfel, W. R.

S. Maiti, J. B. Shear, R. M. Wolliams, W. R. Zipfel, and W. W. Webb, "Measuring Serotonin Distribution in Live Cells with Three-Photon Excitation," Science 275, 530-532 (1997).
[CrossRef] [PubMed]

Biophys. J.

H. Szmacinski and I. Gryczynski, "Three-photon induced fluorescence of the calcium probe Indo-1," Biophys. J. 70, 547-555 (1996).
[CrossRef] [PubMed]

Chem. Phys. Lett.

F. E. Hernández, K. D. Belfield, and I. Cohanoschi, "Three-photon absorption enhancement in a symmetrical charge transfer fluorene derivative," Chem. Phys. Lett. 391, 22-26 (2004).
[CrossRef]

D. Wang, C. Zhan, Y. Chen, Y. J. Li, Z. Z. Lu, and Y. X. Nie, "Large optical power limiting induced by three-photon absorption of two stilbazolium-like dyes," Chem. Phys. Lett. 369, 621-626 (2003).
[CrossRef]

I. Cohanoschi, M. García, C. Toro, K. D. Belfield, and F. E. Hernández, "Three-photon absorption of a new series of halogenated fluorene derivatives," Chem. Phys. Lett. 430, 133-138 (2006).
[CrossRef]

P. Cronstrand, Y. Luo, P. Norman, and H. Agren, "Ab initio calculations of three-photon absorption," Chem. Phys. Lett. 375, 233-239 (2003).
[CrossRef]

J. Chem. Phys.

I. Cohanoschi, K. D. Belfied, C. Toro, and F. E. Hernández, "Solvent effects on the three-photon absorption cross-section of a highly conjugated fluorene derivative," J. Chem. Phys. 125, 161102 (2006).
[CrossRef] [PubMed]

J. Mod. Opt.

Y. Mao, J. Liu, W. Ma, Y. Wu, and Y. Cheng, "Three-photon absorption-induced fluorescence and optical limiting effects in a fluorene derivative," J. Mod. Opt. 54, 77-84 (2007).
[CrossRef]

J. Org. Chem.

K. D. Belfield, K. J. Schafer, W. Mourad, and B. A. Reinhardt, "Synthesis of New Two-Photon Absorbing Fluorene Derivatives via Cu-Mediated Ullmann Condensations," J. Org. Chem. 65, 4475-4481 (2000).
[CrossRef] [PubMed]

Nature

G. S. He, P. P. Markowicz, T. Lin, and P. N. Prasad, "Observation of stimulated emission by direct three-photon excitation," Nature 415, 767-770 (2002).
[CrossRef] [PubMed]

Opt. Lett.

Phys. Rev. A

V. Kimberg, S. Polyutov, F. Gel’mukhanov, and H. Ågren, "Dynamics of cavityless lasing generated by ultrafast multiphoton excitation," Phys. Rev. A 74, 033814 (2006).
[CrossRef]

Phys. Rev. Lett.

S. Singh and L. T. Bradley, "Three-Photon Absorption in Naphthalene Crystals by Laser Excitation," Phys. Rev. Lett. 12, 612-614 (1964).
[CrossRef]

Science

S. Maiti, J. B. Shear, R. M. Wolliams, W. R. Zipfel, and W. W. Webb, "Measuring Serotonin Distribution in Live Cells with Three-Photon Excitation," Science 275, 530-532 (1997).
[CrossRef] [PubMed]

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Figures (4)

Fig. 1.
Fig. 1.

Linear absorption (solid line) and steady fluorescence spectra (dot) of the molecule in DMF at 2×10-5 mol/L. The molecular structure of the solute is given in the top-right corner.

Fig. 2.
Fig. 2.

Cubic dependence of the 3PA induced fluorescence intensity vs incident intensity at 1064 nm for this compound in DMF. The solid line is the best-fitted curve based on the functiony=axn with the best-fitted exponent n=2.98.

Fig. 3.
Fig. 3.

Transmitted on-axis intensity vs. incident on-axis intensity curves of the compound at 0.028 mol/L, fittings using the above method. The dash dot line are the best-fit curve with γ=0. The solid line represent the theoretical fitting. The best-fit parameters was γ=41.2×10-20 cm3/W2

Fig. 4.
Fig. 4.

Nonlinear transmittance versus incident intensity at 1064 nm for the compound in DMF at 0.028 mol/L.

Tables (1)

Tables Icon

Table 1. Electronic transition data obtained by the TD SCF/DFT semi-empirical method for the two molecules at the AM1 optimized geometry.

Equations (6)

Equations on this page are rendered with MathJax. Learn more.

d I ( z , r , t ) d z = γ I ( z , r , t ) 3
I ( L , r , t ) = I ( z = 0 , r , t ) 1 + 2 γ L I 2 ( z = 0 , r , t )
I ( i , j , t ) = I ( i , j , t ) 1 + 2 γ L I 2 ( i , j , t )
I ( i , j + 1 , t ) = S ( i , j ) S ( i , j + 1 ) I ( i , j , t )
T = i = 1 i = n I ( i , m , t ) S ( i , m ) t p i = 1 i = n I ( i , 1 , t ) S ( i , 1 ) t p
σ 3 = γ N A · d 0 × 10 3 ( h · c λ )

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