Abstract

The use of dendritic nanoboxes (DBoxes) to protect encapsulated dye molecules against photodegradation was evaluated. We focused on photoinduced oxidation and studied the ability of DBoxes to protect the dyes inside from reactive singlet oxygen. Rubrene and α-terthienyl were used as the probe and the generator for singlet oxygen, respectively. Bleaching of encapsulated rubrene in a DBox was 50 times slower than that of rubrene alone. Stability was further improved by attachment of singlet-oxygen-quencher molecules to the surfaces of the DBoxes.

© 2002 Optical Society of America

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    [CrossRef]
  2. P. N. Prasad and D. J. Williams, Introduction to Nonlinear Optical Effects in Molecules & Polymers (Wiley, New York, 1991).
  3. M. Mortazavi, H. Yoon, and C. Teng, J. Appl. Phys. 74, 4871 (1993).
    [CrossRef]
  4. M. Cha, W. Torruellas, G. Stegeman, and W. Horsthuis, Appl. Phys. Lett. 65, 2648 (1994).
    [CrossRef]
  5. Q. Zhang, M. Canva, and G. Stegeman, Appl. Phys. Lett. 73, 912 (1998).
    [CrossRef]
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    [CrossRef]
  7. A. Galvan-Gonzalez, K. D. Belfield, G. I. Stegeman, M. Canva, K.-P. Chan, K. Park, L. Sukhomlinova, and R. J. Twieg, Appl. Phys. Lett. 77, 2083 (2000).
    [CrossRef]
  8. A. Adronov and J. M. J. Fréchet, Chem. Commun. 18, 1701 (2000).
    [CrossRef]
  9. H. Ma and A. K.-Y. Jen, Adv. Mater. 13, 1201 (2001).
    [CrossRef]
  10. H.-F. Chow, T. K. -K. Mong, M. F. Nongrum, and C.-W. Wan, Tetrahedron 54, 8543 (1998).
    [CrossRef]
  11. G. R. Newkome, E. He, and C. N. Moorefield, Chem. Rev. 99, 1689 (1999).
    [CrossRef]
  12. A. Archut and F. Vögtle, Chem. Soc. Rev. 27, 233 (1999).
    [CrossRef]
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    [CrossRef] [PubMed]
  14. J. F. G. A. Jansen, E. W. Meijer, and E. M. M. de Brabander-van den Berg, J. Am. Chem. Soc. 117, 4417 (1995).
    [CrossRef]
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    [CrossRef]
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    [CrossRef]
  17. A. Otomo, “Design and fabrication of channel waveguides in a 4-dimethylamino-4′-nitrostilbene side chain polymer,” M.S. thesis (University of Central Florida, Orlando, Fla., 1993).
  18. A. Otomo, G. I. Stegeman, W. Horsthuis, and G. Möhlmann, in Polymers for Second-Order Nonlinear Optics, G. A. Lindsay and K. D. Singer, eds., Vol. 601 of ACS Symposium Series (American Chemical Society, Washington, D.C., 1995), pp. 469–483.
    [CrossRef]
  19. A. Dubois, M. Canva, A. Brun, F. Chaput, and J.-P. Boilot, Appl. Opt. 35, 3193 (1996).
    [CrossRef] [PubMed]

2001

H. Ma and A. K.-Y. Jen, Adv. Mater. 13, 1201 (2001).
[CrossRef]

2000

A. Galvan-Gonzalez, K. D. Belfield, G. I. Stegeman, M. Canva, K.-P. Chan, K. Park, L. Sukhomlinova, and R. J. Twieg, Appl. Phys. Lett. 77, 2083 (2000).
[CrossRef]

A. Adronov and J. M. J. Fréchet, Chem. Commun. 18, 1701 (2000).
[CrossRef]

1999

G. R. Newkome, E. He, and C. N. Moorefield, Chem. Rev. 99, 1689 (1999).
[CrossRef]

A. Archut and F. Vögtle, Chem. Soc. Rev. 27, 233 (1999).
[CrossRef]

1998

H.-F. Chow, T. K. -K. Mong, M. F. Nongrum, and C.-W. Wan, Tetrahedron 54, 8543 (1998).
[CrossRef]

Q. Zhang, M. Canva, and G. Stegeman, Appl. Phys. Lett. 73, 912 (1998).
[CrossRef]

1997

P. Miklis, T. Çagin, and W. A. Goddard, J. Am. Chem. Soc. 119, 7458 (1997).
[CrossRef]

1996

1995

J. F. G. A. Jansen, E. W. Meijer, and E. M. M. de Brabander-van den Berg, J. Am. Chem. Soc. 117, 4417 (1995).
[CrossRef]

1994

J. F. G. A. Jansen, E. M. M. de Brabander-van den Berg, and E. W. Meijer, Science 266, 1226 (1994).
[CrossRef] [PubMed]

M. Cha, W. Torruellas, G. Stegeman, and W. Horsthuis, Appl. Phys. Lett. 65, 2648 (1994).
[CrossRef]

1993

M. Mortazavi, H. Yoon, and C. Teng, J. Appl. Phys. 74, 4871 (1993).
[CrossRef]

1987

J. C. Scaiano, A. MacEachern, J. T. Arnason, P. Morand, and D. Weir, Photochem. Photobiol. 46, 193 (1987).
[CrossRef]

Adronov, A.

A. Adronov and J. M. J. Fréchet, Chem. Commun. 18, 1701 (2000).
[CrossRef]

Archut, A.

A. Archut and F. Vögtle, Chem. Soc. Rev. 27, 233 (1999).
[CrossRef]

Arnason, J. T.

J. C. Scaiano, A. MacEachern, J. T. Arnason, P. Morand, and D. Weir, Photochem. Photobiol. 46, 193 (1987).
[CrossRef]

Belfield, K. D.

A. Galvan-Gonzalez, K. D. Belfield, G. I. Stegeman, M. Canva, K.-P. Chan, K. Park, L. Sukhomlinova, and R. J. Twieg, Appl. Phys. Lett. 77, 2083 (2000).
[CrossRef]

Boilot, J.-P.

Brun, A.

Çagin, T.

P. Miklis, T. Çagin, and W. A. Goddard, J. Am. Chem. Soc. 119, 7458 (1997).
[CrossRef]

Canva, M.

A. Galvan-Gonzalez, K. D. Belfield, G. I. Stegeman, M. Canva, K.-P. Chan, K. Park, L. Sukhomlinova, and R. J. Twieg, Appl. Phys. Lett. 77, 2083 (2000).
[CrossRef]

Q. Zhang, M. Canva, and G. Stegeman, Appl. Phys. Lett. 73, 912 (1998).
[CrossRef]

A. Dubois, M. Canva, A. Brun, F. Chaput, and J.-P. Boilot, Appl. Opt. 35, 3193 (1996).
[CrossRef] [PubMed]

Cha, M.

M. Cha, W. Torruellas, G. Stegeman, and W. Horsthuis, Appl. Phys. Lett. 65, 2648 (1994).
[CrossRef]

Chan, K.-P.

A. Galvan-Gonzalez, K. D. Belfield, G. I. Stegeman, M. Canva, K.-P. Chan, K. Park, L. Sukhomlinova, and R. J. Twieg, Appl. Phys. Lett. 77, 2083 (2000).
[CrossRef]

Chaput, F.

Chow, H.-F.

H.-F. Chow, T. K. -K. Mong, M. F. Nongrum, and C.-W. Wan, Tetrahedron 54, 8543 (1998).
[CrossRef]

de Brabander-van den Berg, E. M. M.

J. F. G. A. Jansen, E. W. Meijer, and E. M. M. de Brabander-van den Berg, J. Am. Chem. Soc. 117, 4417 (1995).
[CrossRef]

J. F. G. A. Jansen, E. M. M. de Brabander-van den Berg, and E. W. Meijer, Science 266, 1226 (1994).
[CrossRef] [PubMed]

Drexhage, K. H.

K. H. Drexhage, in Dye Lasers, F. P. Schäfer, ed., Vol. 1 of Springer Topics in Applied Physics (Springer-Verlag, Berlin, 1973), pp. 144–193.
[CrossRef]

Dubois, A.

Fréchet, J. M. J.

A. Adronov and J. M. J. Fréchet, Chem. Commun. 18, 1701 (2000).
[CrossRef]

Galvan-Gonzalez, A.

A. Galvan-Gonzalez, K. D. Belfield, G. I. Stegeman, M. Canva, K.-P. Chan, K. Park, L. Sukhomlinova, and R. J. Twieg, Appl. Phys. Lett. 77, 2083 (2000).
[CrossRef]

Goddard, W. A.

P. Miklis, T. Çagin, and W. A. Goddard, J. Am. Chem. Soc. 119, 7458 (1997).
[CrossRef]

He, E.

G. R. Newkome, E. He, and C. N. Moorefield, Chem. Rev. 99, 1689 (1999).
[CrossRef]

Horsthuis, W.

M. Cha, W. Torruellas, G. Stegeman, and W. Horsthuis, Appl. Phys. Lett. 65, 2648 (1994).
[CrossRef]

A. Otomo, G. I. Stegeman, W. Horsthuis, and G. Möhlmann, in Polymers for Second-Order Nonlinear Optics, G. A. Lindsay and K. D. Singer, eds., Vol. 601 of ACS Symposium Series (American Chemical Society, Washington, D.C., 1995), pp. 469–483.
[CrossRef]

Jansen, J. F. G. A.

J. F. G. A. Jansen, E. W. Meijer, and E. M. M. de Brabander-van den Berg, J. Am. Chem. Soc. 117, 4417 (1995).
[CrossRef]

J. F. G. A. Jansen, E. M. M. de Brabander-van den Berg, and E. W. Meijer, Science 266, 1226 (1994).
[CrossRef] [PubMed]

Jen, A. K.-Y.

H. Ma and A. K.-Y. Jen, Adv. Mater. 13, 1201 (2001).
[CrossRef]

Jones, G.

G. Jones, in Dye Laser Principles with Applications, F. J. Duarte and L. W. Hillman, eds. (Academic, San Diego, Calif., 1990), pp. 287–343.
[CrossRef]

Ma, H.

H. Ma and A. K.-Y. Jen, Adv. Mater. 13, 1201 (2001).
[CrossRef]

MacEachern, A.

J. C. Scaiano, A. MacEachern, J. T. Arnason, P. Morand, and D. Weir, Photochem. Photobiol. 46, 193 (1987).
[CrossRef]

Meijer, E. W.

J. F. G. A. Jansen, E. W. Meijer, and E. M. M. de Brabander-van den Berg, J. Am. Chem. Soc. 117, 4417 (1995).
[CrossRef]

J. F. G. A. Jansen, E. M. M. de Brabander-van den Berg, and E. W. Meijer, Science 266, 1226 (1994).
[CrossRef] [PubMed]

Miklis, P.

P. Miklis, T. Çagin, and W. A. Goddard, J. Am. Chem. Soc. 119, 7458 (1997).
[CrossRef]

Möhlmann, G.

A. Otomo, G. I. Stegeman, W. Horsthuis, and G. Möhlmann, in Polymers for Second-Order Nonlinear Optics, G. A. Lindsay and K. D. Singer, eds., Vol. 601 of ACS Symposium Series (American Chemical Society, Washington, D.C., 1995), pp. 469–483.
[CrossRef]

Mong, T. K. -K.

H.-F. Chow, T. K. -K. Mong, M. F. Nongrum, and C.-W. Wan, Tetrahedron 54, 8543 (1998).
[CrossRef]

Moorefield, C. N.

G. R. Newkome, E. He, and C. N. Moorefield, Chem. Rev. 99, 1689 (1999).
[CrossRef]

Morand, P.

J. C. Scaiano, A. MacEachern, J. T. Arnason, P. Morand, and D. Weir, Photochem. Photobiol. 46, 193 (1987).
[CrossRef]

Mortazavi, M.

M. Mortazavi, H. Yoon, and C. Teng, J. Appl. Phys. 74, 4871 (1993).
[CrossRef]

Newkome, G. R.

G. R. Newkome, E. He, and C. N. Moorefield, Chem. Rev. 99, 1689 (1999).
[CrossRef]

Nongrum, M. F.

H.-F. Chow, T. K. -K. Mong, M. F. Nongrum, and C.-W. Wan, Tetrahedron 54, 8543 (1998).
[CrossRef]

Otomo, A.

A. Otomo, “Design and fabrication of channel waveguides in a 4-dimethylamino-4′-nitrostilbene side chain polymer,” M.S. thesis (University of Central Florida, Orlando, Fla., 1993).

A. Otomo, G. I. Stegeman, W. Horsthuis, and G. Möhlmann, in Polymers for Second-Order Nonlinear Optics, G. A. Lindsay and K. D. Singer, eds., Vol. 601 of ACS Symposium Series (American Chemical Society, Washington, D.C., 1995), pp. 469–483.
[CrossRef]

Park, K.

A. Galvan-Gonzalez, K. D. Belfield, G. I. Stegeman, M. Canva, K.-P. Chan, K. Park, L. Sukhomlinova, and R. J. Twieg, Appl. Phys. Lett. 77, 2083 (2000).
[CrossRef]

Prasad, P. N.

P. N. Prasad and D. J. Williams, Introduction to Nonlinear Optical Effects in Molecules & Polymers (Wiley, New York, 1991).

Scaiano, J. C.

J. C. Scaiano, A. MacEachern, J. T. Arnason, P. Morand, and D. Weir, Photochem. Photobiol. 46, 193 (1987).
[CrossRef]

Stegeman, G.

Q. Zhang, M. Canva, and G. Stegeman, Appl. Phys. Lett. 73, 912 (1998).
[CrossRef]

M. Cha, W. Torruellas, G. Stegeman, and W. Horsthuis, Appl. Phys. Lett. 65, 2648 (1994).
[CrossRef]

Stegeman, G. I.

A. Galvan-Gonzalez, K. D. Belfield, G. I. Stegeman, M. Canva, K.-P. Chan, K. Park, L. Sukhomlinova, and R. J. Twieg, Appl. Phys. Lett. 77, 2083 (2000).
[CrossRef]

A. Otomo, G. I. Stegeman, W. Horsthuis, and G. Möhlmann, in Polymers for Second-Order Nonlinear Optics, G. A. Lindsay and K. D. Singer, eds., Vol. 601 of ACS Symposium Series (American Chemical Society, Washington, D.C., 1995), pp. 469–483.
[CrossRef]

Sukhomlinova, L.

A. Galvan-Gonzalez, K. D. Belfield, G. I. Stegeman, M. Canva, K.-P. Chan, K. Park, L. Sukhomlinova, and R. J. Twieg, Appl. Phys. Lett. 77, 2083 (2000).
[CrossRef]

Teng, C.

M. Mortazavi, H. Yoon, and C. Teng, J. Appl. Phys. 74, 4871 (1993).
[CrossRef]

Torruellas, W.

M. Cha, W. Torruellas, G. Stegeman, and W. Horsthuis, Appl. Phys. Lett. 65, 2648 (1994).
[CrossRef]

Twieg, R. J.

A. Galvan-Gonzalez, K. D. Belfield, G. I. Stegeman, M. Canva, K.-P. Chan, K. Park, L. Sukhomlinova, and R. J. Twieg, Appl. Phys. Lett. 77, 2083 (2000).
[CrossRef]

Vögtle, F.

A. Archut and F. Vögtle, Chem. Soc. Rev. 27, 233 (1999).
[CrossRef]

Wan, C.-W.

H.-F. Chow, T. K. -K. Mong, M. F. Nongrum, and C.-W. Wan, Tetrahedron 54, 8543 (1998).
[CrossRef]

Weir, D.

J. C. Scaiano, A. MacEachern, J. T. Arnason, P. Morand, and D. Weir, Photochem. Photobiol. 46, 193 (1987).
[CrossRef]

Williams, D. J.

P. N. Prasad and D. J. Williams, Introduction to Nonlinear Optical Effects in Molecules & Polymers (Wiley, New York, 1991).

Yoon, H.

M. Mortazavi, H. Yoon, and C. Teng, J. Appl. Phys. 74, 4871 (1993).
[CrossRef]

Zhang, Q.

Q. Zhang, M. Canva, and G. Stegeman, Appl. Phys. Lett. 73, 912 (1998).
[CrossRef]

Adv. Mater.

H. Ma and A. K.-Y. Jen, Adv. Mater. 13, 1201 (2001).
[CrossRef]

Appl. Opt.

Appl. Phys. Lett.

A. Galvan-Gonzalez, K. D. Belfield, G. I. Stegeman, M. Canva, K.-P. Chan, K. Park, L. Sukhomlinova, and R. J. Twieg, Appl. Phys. Lett. 77, 2083 (2000).
[CrossRef]

M. Cha, W. Torruellas, G. Stegeman, and W. Horsthuis, Appl. Phys. Lett. 65, 2648 (1994).
[CrossRef]

Q. Zhang, M. Canva, and G. Stegeman, Appl. Phys. Lett. 73, 912 (1998).
[CrossRef]

Chem. Commun.

A. Adronov and J. M. J. Fréchet, Chem. Commun. 18, 1701 (2000).
[CrossRef]

Chem. Rev.

G. R. Newkome, E. He, and C. N. Moorefield, Chem. Rev. 99, 1689 (1999).
[CrossRef]

Chem. Soc. Rev.

A. Archut and F. Vögtle, Chem. Soc. Rev. 27, 233 (1999).
[CrossRef]

J. Am. Chem. Soc.

J. F. G. A. Jansen, E. W. Meijer, and E. M. M. de Brabander-van den Berg, J. Am. Chem. Soc. 117, 4417 (1995).
[CrossRef]

P. Miklis, T. Çagin, and W. A. Goddard, J. Am. Chem. Soc. 119, 7458 (1997).
[CrossRef]

J. Appl. Phys.

M. Mortazavi, H. Yoon, and C. Teng, J. Appl. Phys. 74, 4871 (1993).
[CrossRef]

Photochem. Photobiol.

J. C. Scaiano, A. MacEachern, J. T. Arnason, P. Morand, and D. Weir, Photochem. Photobiol. 46, 193 (1987).
[CrossRef]

Science

J. F. G. A. Jansen, E. M. M. de Brabander-van den Berg, and E. W. Meijer, Science 266, 1226 (1994).
[CrossRef] [PubMed]

Tetrahedron

H.-F. Chow, T. K. -K. Mong, M. F. Nongrum, and C.-W. Wan, Tetrahedron 54, 8543 (1998).
[CrossRef]

Other

G. Jones, in Dye Laser Principles with Applications, F. J. Duarte and L. W. Hillman, eds. (Academic, San Diego, Calif., 1990), pp. 287–343.
[CrossRef]

K. H. Drexhage, in Dye Lasers, F. P. Schäfer, ed., Vol. 1 of Springer Topics in Applied Physics (Springer-Verlag, Berlin, 1973), pp. 144–193.
[CrossRef]

P. N. Prasad and D. J. Williams, Introduction to Nonlinear Optical Effects in Molecules & Polymers (Wiley, New York, 1991).

A. Otomo, “Design and fabrication of channel waveguides in a 4-dimethylamino-4′-nitrostilbene side chain polymer,” M.S. thesis (University of Central Florida, Orlando, Fla., 1993).

A. Otomo, G. I. Stegeman, W. Horsthuis, and G. Möhlmann, in Polymers for Second-Order Nonlinear Optics, G. A. Lindsay and K. D. Singer, eds., Vol. 601 of ACS Symposium Series (American Chemical Society, Washington, D.C., 1995), pp. 469–483.
[CrossRef]

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Figures (4)

Fig. 1
Fig. 1

Absorption spectra of rubrene (solid curve) and rubrene peroxide (dashed curve) in CH2Cl2.

Fig. 2
Fig. 2

Molecular structure of dendrimer and surface molecules.

Fig. 3
Fig. 3

Probe-beam transmissions as functions of exposure time for naked rubrene solutions with (crosses) and without (open circles) αT. The dashed curves correspond to fits with Eq. (1).

Fig. 4
Fig. 4

Probe-beam transmission as a function of exposure time for encapsulated rubrene in the tBOC-l-Phe DBox.

Tables (1)

Tables Icon

Table 1 Relative β Factors of Different Rubrene Solutions

Equations (1)

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Tt=T1+T/T0-1exp-βIt.

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