Abstract

We have designed an original approach for efficient Second Harmonic Generation of tailored V-shape benzo[b]thiophene molecular systems enabling versatile and flexible one-step, dry and technologically friendly thin film processing. The designed moieties show χ (2) values at least as high as the reference LiNbO3 single crystal, without poling processing and matching the constrains of integrated optical configuration for nonlinear optical devices. This may open the way to a new class of organic materials exploitable for photonic applications.

© 2009 Optical Society of America

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    [Crossref]
  7. L. R. Dalton, “Nonlinear Optical Polymeric Materials,” in Advances in Polymer Science 158, Springer-Verlag, Heidelberg, 2001, p. 1–86.
  8. D. Gonin and C. Noël, Liquid Crystalline Polymers, in Organic Thin Films for Waveguiding Nonlinear Optics, F. Kajzar and J. Swalen Eds, Gordon & Breach Sc. Publ., Amsterdam1996, pp.221–288.
  9. J. Le Moigne, in Organic Thin Films for Waveguiding Nonlinear Optics F. Kajzar and J. Swalen Eds, Gordon & Breach Sc. Publ., Amsterdam1996, pp. 289–327.
  10. A. Facchetti, E. Annoni, L. Beverina, L. Beverina, M. Morone, P. Zhu, T. J. Marks, and G. A. Pagani, ”Very large electro-optic responses in H-bonded heteroaromatic films grown by physical vapour deposition”, Nat. Mater. 3, 910–917 (2004).
    [Crossref] [PubMed]
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    [Crossref]
  12. C.R Moylan, S Ermer, S.M. Lovejoy, I.-H. McComb, D.S. Leung, R. Wortmann, P. Krdmer, and R.J. Twieg, “Dicyanomethylene)pyran derivatives with C2v symmetry: An unusual class of nonlinear optical chromophores.” JACS 118, 12950–12955 (1996)
    [Crossref]
  13. Victor Ostroverkhov, Kenneth D. Singer, and Rolfe G. Petschek, “Second-order nonlinear optical processes in non-polar chiral materials: relationship between molecular and macroscopic properties,” J. Opt. Soc. Am B. 18, 1858–1865 (2001).
    [Crossref]
  14. V. Ostroverkhov, R.G. Petschek, K.D. Singer, and R.J. Twieg, “Lambda-Shaped Chromophores for Chiral Nonlinear Optical Materials,” Chem. Phys. Lett. 340, 109–115 (2001).
    [Crossref]
  15. T. Watanabe, H. Yamammoto, T. Hosomin, and S. Miyata, in Organic Molecules for Nonlinear Optics and Photonics, J. Messier, F. Kajzar, and P. Prasad, Eds, Kluwer Acad. Publ., Dordrecht (1991).
  16. Giovanna Barbarella, Laura Favaretto, Alberto Zanelli, Giuseppe Gigli, Marco Mazzeo, Marco Anni, and Alessandro Bongini, “V-shaped thiophene based oligomers with improved electroluminescence properties,” Adv. Funct. Mater. 15, 664–670 (2005).
    [Crossref]
  17. Marco Mazzeo, Vincenzo Vitale, Fabio Della Sala, Dario Pisignano, Marco Anni, Giovanna Barbarella, Laura Favaretto, Alberto Zanelli, Roberto Cingolani, and Giuseppe Gigli, “New branched thiophene-based oligomers for bright organic light emitting devices,” Adv. Mater. 15, 2060–2063 (2003).
    [Crossref]
  18. K. D. Singer, J. E. Sohn, and S. J. Lalama, Second harmonic generation in poled polymer films, Appl. Phys. Lett. 49, 248 (1986)
    [Crossref]
  19. J. Swalen and F. Kajzar, Introduction, in Organic Thin Films for Waveguiding Nonlinear Optics, F. Kajzar and J. Swalen Eds, Gordon & Breach Sc. Publ., Amsterdam1996, pp. 1–85

2005 (1)

Giovanna Barbarella, Laura Favaretto, Alberto Zanelli, Giuseppe Gigli, Marco Mazzeo, Marco Anni, and Alessandro Bongini, “V-shaped thiophene based oligomers with improved electroluminescence properties,” Adv. Funct. Mater. 15, 664–670 (2005).
[Crossref]

2004 (1)

A. Facchetti, E. Annoni, L. Beverina, L. Beverina, M. Morone, P. Zhu, T. J. Marks, and G. A. Pagani, ”Very large electro-optic responses in H-bonded heteroaromatic films grown by physical vapour deposition”, Nat. Mater. 3, 910–917 (2004).
[Crossref] [PubMed]

2003 (1)

Marco Mazzeo, Vincenzo Vitale, Fabio Della Sala, Dario Pisignano, Marco Anni, Giovanna Barbarella, Laura Favaretto, Alberto Zanelli, Roberto Cingolani, and Giuseppe Gigli, “New branched thiophene-based oligomers for bright organic light emitting devices,” Adv. Mater. 15, 2060–2063 (2003).
[Crossref]

2001 (3)

Victor Ostroverkhov, Kenneth D. Singer, and Rolfe G. Petschek, “Second-order nonlinear optical processes in non-polar chiral materials: relationship between molecular and macroscopic properties,” J. Opt. Soc. Am B. 18, 1858–1865 (2001).
[Crossref]

V. Ostroverkhov, R.G. Petschek, K.D. Singer, and R.J. Twieg, “Lambda-Shaped Chromophores for Chiral Nonlinear Optical Materials,” Chem. Phys. Lett. 340, 109–115 (2001).
[Crossref]

F. Kajzar, Y. Okada-Shudo, C. Meritt, and Z. Kafafi, “Second- and third-order non-linear optical properties of multilayered structures and composites of C60 with electron donors,” Synth. Met. 117, 189–193 (2001).
[Crossref]

1996 (1)

C.R Moylan, S Ermer, S.M. Lovejoy, I.-H. McComb, D.S. Leung, R. Wortmann, P. Krdmer, and R.J. Twieg, “Dicyanomethylene)pyran derivatives with C2v symmetry: An unusual class of nonlinear optical chromophores.” JACS 118, 12950–12955 (1996)
[Crossref]

1992 (1)

Ch. Bosshard, M. Küpfer, M. Flörsheimer, Th. Borer, P. Günter, Q. Tang, and S. Zahir, “Investigation of chromophore orientation of 2-docosylamino-5-nitropyridine and derivatives by nonlinear optical techniques,” Thin Solid Films 210/211, 198–201 (1992)]
[Crossref]

1986 (1)

K. D. Singer, J. E. Sohn, and S. J. Lalama, Second harmonic generation in poled polymer films, Appl. Phys. Lett. 49, 248 (1986)
[Crossref]

1977 (1)

J. L. Oudar and D. S. Chemla, “Hyperpolarizabilities of nitroanilines and their relations to the excited state dipole moment,” J. Chem. Phys 66, 2664–2667 (1977).
[Crossref]

Anni, Marco

Giovanna Barbarella, Laura Favaretto, Alberto Zanelli, Giuseppe Gigli, Marco Mazzeo, Marco Anni, and Alessandro Bongini, “V-shaped thiophene based oligomers with improved electroluminescence properties,” Adv. Funct. Mater. 15, 664–670 (2005).
[Crossref]

Marco Mazzeo, Vincenzo Vitale, Fabio Della Sala, Dario Pisignano, Marco Anni, Giovanna Barbarella, Laura Favaretto, Alberto Zanelli, Roberto Cingolani, and Giuseppe Gigli, “New branched thiophene-based oligomers for bright organic light emitting devices,” Adv. Mater. 15, 2060–2063 (2003).
[Crossref]

Annoni, E.

A. Facchetti, E. Annoni, L. Beverina, L. Beverina, M. Morone, P. Zhu, T. J. Marks, and G. A. Pagani, ”Very large electro-optic responses in H-bonded heteroaromatic films grown by physical vapour deposition”, Nat. Mater. 3, 910–917 (2004).
[Crossref] [PubMed]

Barbarella, Giovanna

Giovanna Barbarella, Laura Favaretto, Alberto Zanelli, Giuseppe Gigli, Marco Mazzeo, Marco Anni, and Alessandro Bongini, “V-shaped thiophene based oligomers with improved electroluminescence properties,” Adv. Funct. Mater. 15, 664–670 (2005).
[Crossref]

Marco Mazzeo, Vincenzo Vitale, Fabio Della Sala, Dario Pisignano, Marco Anni, Giovanna Barbarella, Laura Favaretto, Alberto Zanelli, Roberto Cingolani, and Giuseppe Gigli, “New branched thiophene-based oligomers for bright organic light emitting devices,” Adv. Mater. 15, 2060–2063 (2003).
[Crossref]

Beverina, L.

A. Facchetti, E. Annoni, L. Beverina, L. Beverina, M. Morone, P. Zhu, T. J. Marks, and G. A. Pagani, ”Very large electro-optic responses in H-bonded heteroaromatic films grown by physical vapour deposition”, Nat. Mater. 3, 910–917 (2004).
[Crossref] [PubMed]

A. Facchetti, E. Annoni, L. Beverina, L. Beverina, M. Morone, P. Zhu, T. J. Marks, and G. A. Pagani, ”Very large electro-optic responses in H-bonded heteroaromatic films grown by physical vapour deposition”, Nat. Mater. 3, 910–917 (2004).
[Crossref] [PubMed]

Bongini, Alessandro

Giovanna Barbarella, Laura Favaretto, Alberto Zanelli, Giuseppe Gigli, Marco Mazzeo, Marco Anni, and Alessandro Bongini, “V-shaped thiophene based oligomers with improved electroluminescence properties,” Adv. Funct. Mater. 15, 664–670 (2005).
[Crossref]

Borer, Th.

Ch. Bosshard, M. Küpfer, M. Flörsheimer, Th. Borer, P. Günter, Q. Tang, and S. Zahir, “Investigation of chromophore orientation of 2-docosylamino-5-nitropyridine and derivatives by nonlinear optical techniques,” Thin Solid Films 210/211, 198–201 (1992)]
[Crossref]

Bosshard, Ch.

Ch. Bosshard, M. Küpfer, M. Flörsheimer, Th. Borer, P. Günter, Q. Tang, and S. Zahir, “Investigation of chromophore orientation of 2-docosylamino-5-nitropyridine and derivatives by nonlinear optical techniques,” Thin Solid Films 210/211, 198–201 (1992)]
[Crossref]

Chemla, D. S.

J. L. Oudar and D. S. Chemla, “Hyperpolarizabilities of nitroanilines and their relations to the excited state dipole moment,” J. Chem. Phys 66, 2664–2667 (1977).
[Crossref]

Cingolani, Roberto

Marco Mazzeo, Vincenzo Vitale, Fabio Della Sala, Dario Pisignano, Marco Anni, Giovanna Barbarella, Laura Favaretto, Alberto Zanelli, Roberto Cingolani, and Giuseppe Gigli, “New branched thiophene-based oligomers for bright organic light emitting devices,” Adv. Mater. 15, 2060–2063 (2003).
[Crossref]

Dalton, L. R.

L. R. Dalton, “Nonlinear Optical Polymeric Materials,” in Advances in Polymer Science 158, Springer-Verlag, Heidelberg, 2001, p. 1–86.

Ermer, S

C.R Moylan, S Ermer, S.M. Lovejoy, I.-H. McComb, D.S. Leung, R. Wortmann, P. Krdmer, and R.J. Twieg, “Dicyanomethylene)pyran derivatives with C2v symmetry: An unusual class of nonlinear optical chromophores.” JACS 118, 12950–12955 (1996)
[Crossref]

Facchetti, A.

A. Facchetti, E. Annoni, L. Beverina, L. Beverina, M. Morone, P. Zhu, T. J. Marks, and G. A. Pagani, ”Very large electro-optic responses in H-bonded heteroaromatic films grown by physical vapour deposition”, Nat. Mater. 3, 910–917 (2004).
[Crossref] [PubMed]

Favaretto, Laura

Giovanna Barbarella, Laura Favaretto, Alberto Zanelli, Giuseppe Gigli, Marco Mazzeo, Marco Anni, and Alessandro Bongini, “V-shaped thiophene based oligomers with improved electroluminescence properties,” Adv. Funct. Mater. 15, 664–670 (2005).
[Crossref]

Marco Mazzeo, Vincenzo Vitale, Fabio Della Sala, Dario Pisignano, Marco Anni, Giovanna Barbarella, Laura Favaretto, Alberto Zanelli, Roberto Cingolani, and Giuseppe Gigli, “New branched thiophene-based oligomers for bright organic light emitting devices,” Adv. Mater. 15, 2060–2063 (2003).
[Crossref]

Flörsheimer, M.

Ch. Bosshard, M. Küpfer, M. Flörsheimer, Th. Borer, P. Günter, Q. Tang, and S. Zahir, “Investigation of chromophore orientation of 2-docosylamino-5-nitropyridine and derivatives by nonlinear optical techniques,” Thin Solid Films 210/211, 198–201 (1992)]
[Crossref]

Gigli, Giuseppe

Giovanna Barbarella, Laura Favaretto, Alberto Zanelli, Giuseppe Gigli, Marco Mazzeo, Marco Anni, and Alessandro Bongini, “V-shaped thiophene based oligomers with improved electroluminescence properties,” Adv. Funct. Mater. 15, 664–670 (2005).
[Crossref]

Marco Mazzeo, Vincenzo Vitale, Fabio Della Sala, Dario Pisignano, Marco Anni, Giovanna Barbarella, Laura Favaretto, Alberto Zanelli, Roberto Cingolani, and Giuseppe Gigli, “New branched thiophene-based oligomers for bright organic light emitting devices,” Adv. Mater. 15, 2060–2063 (2003).
[Crossref]

Gonin, D.

D. Gonin and C. Noël, Liquid Crystalline Polymers, in Organic Thin Films for Waveguiding Nonlinear Optics, F. Kajzar and J. Swalen Eds, Gordon & Breach Sc. Publ., Amsterdam1996, pp.221–288.

Günter, P.

Ch. Bosshard, M. Küpfer, M. Flörsheimer, Th. Borer, P. Günter, Q. Tang, and S. Zahir, “Investigation of chromophore orientation of 2-docosylamino-5-nitropyridine and derivatives by nonlinear optical techniques,” Thin Solid Films 210/211, 198–201 (1992)]
[Crossref]

Hosomin, T.

T. Watanabe, H. Yamammoto, T. Hosomin, and S. Miyata, in Organic Molecules for Nonlinear Optics and Photonics, J. Messier, F. Kajzar, and P. Prasad, Eds, Kluwer Acad. Publ., Dordrecht (1991).

Kafafi, Z.

F. Kajzar, Y. Okada-Shudo, C. Meritt, and Z. Kafafi, “Second- and third-order non-linear optical properties of multilayered structures and composites of C60 with electron donors,” Synth. Met. 117, 189–193 (2001).
[Crossref]

Kajzar, F.

F. Kajzar, Y. Okada-Shudo, C. Meritt, and Z. Kafafi, “Second- and third-order non-linear optical properties of multilayered structures and composites of C60 with electron donors,” Synth. Met. 117, 189–193 (2001).
[Crossref]

J. Swalen and F. Kajzar, Introduction, in Organic Thin Films for Waveguiding Nonlinear Optics, F. Kajzar and J. Swalen Eds, Gordon & Breach Sc. Publ., Amsterdam1996, pp. 1–85

Krdmer, P.

C.R Moylan, S Ermer, S.M. Lovejoy, I.-H. McComb, D.S. Leung, R. Wortmann, P. Krdmer, and R.J. Twieg, “Dicyanomethylene)pyran derivatives with C2v symmetry: An unusual class of nonlinear optical chromophores.” JACS 118, 12950–12955 (1996)
[Crossref]

Küpfer, M.

Ch. Bosshard, M. Küpfer, M. Flörsheimer, Th. Borer, P. Günter, Q. Tang, and S. Zahir, “Investigation of chromophore orientation of 2-docosylamino-5-nitropyridine and derivatives by nonlinear optical techniques,” Thin Solid Films 210/211, 198–201 (1992)]
[Crossref]

Lalama, S. J.

K. D. Singer, J. E. Sohn, and S. J. Lalama, Second harmonic generation in poled polymer films, Appl. Phys. Lett. 49, 248 (1986)
[Crossref]

Leung, D.S.

C.R Moylan, S Ermer, S.M. Lovejoy, I.-H. McComb, D.S. Leung, R. Wortmann, P. Krdmer, and R.J. Twieg, “Dicyanomethylene)pyran derivatives with C2v symmetry: An unusual class of nonlinear optical chromophores.” JACS 118, 12950–12955 (1996)
[Crossref]

Lovejoy, S.M.

C.R Moylan, S Ermer, S.M. Lovejoy, I.-H. McComb, D.S. Leung, R. Wortmann, P. Krdmer, and R.J. Twieg, “Dicyanomethylene)pyran derivatives with C2v symmetry: An unusual class of nonlinear optical chromophores.” JACS 118, 12950–12955 (1996)
[Crossref]

Marks, T. J.

A. Facchetti, E. Annoni, L. Beverina, L. Beverina, M. Morone, P. Zhu, T. J. Marks, and G. A. Pagani, ”Very large electro-optic responses in H-bonded heteroaromatic films grown by physical vapour deposition”, Nat. Mater. 3, 910–917 (2004).
[Crossref] [PubMed]

Mazzeo, Marco

Giovanna Barbarella, Laura Favaretto, Alberto Zanelli, Giuseppe Gigli, Marco Mazzeo, Marco Anni, and Alessandro Bongini, “V-shaped thiophene based oligomers with improved electroluminescence properties,” Adv. Funct. Mater. 15, 664–670 (2005).
[Crossref]

Marco Mazzeo, Vincenzo Vitale, Fabio Della Sala, Dario Pisignano, Marco Anni, Giovanna Barbarella, Laura Favaretto, Alberto Zanelli, Roberto Cingolani, and Giuseppe Gigli, “New branched thiophene-based oligomers for bright organic light emitting devices,” Adv. Mater. 15, 2060–2063 (2003).
[Crossref]

McComb, I.-H.

C.R Moylan, S Ermer, S.M. Lovejoy, I.-H. McComb, D.S. Leung, R. Wortmann, P. Krdmer, and R.J. Twieg, “Dicyanomethylene)pyran derivatives with C2v symmetry: An unusual class of nonlinear optical chromophores.” JACS 118, 12950–12955 (1996)
[Crossref]

Meritt, C.

F. Kajzar, Y. Okada-Shudo, C. Meritt, and Z. Kafafi, “Second- and third-order non-linear optical properties of multilayered structures and composites of C60 with electron donors,” Synth. Met. 117, 189–193 (2001).
[Crossref]

Miyata, S.

T. Watanabe, H. Yamammoto, T. Hosomin, and S. Miyata, in Organic Molecules for Nonlinear Optics and Photonics, J. Messier, F. Kajzar, and P. Prasad, Eds, Kluwer Acad. Publ., Dordrecht (1991).

Moigne, J. Le

J. Le Moigne, in Organic Thin Films for Waveguiding Nonlinear Optics F. Kajzar and J. Swalen Eds, Gordon & Breach Sc. Publ., Amsterdam1996, pp. 289–327.

Morone, M.

A. Facchetti, E. Annoni, L. Beverina, L. Beverina, M. Morone, P. Zhu, T. J. Marks, and G. A. Pagani, ”Very large electro-optic responses in H-bonded heteroaromatic films grown by physical vapour deposition”, Nat. Mater. 3, 910–917 (2004).
[Crossref] [PubMed]

Moylan, C.R

C.R Moylan, S Ermer, S.M. Lovejoy, I.-H. McComb, D.S. Leung, R. Wortmann, P. Krdmer, and R.J. Twieg, “Dicyanomethylene)pyran derivatives with C2v symmetry: An unusual class of nonlinear optical chromophores.” JACS 118, 12950–12955 (1996)
[Crossref]

Noël, C.

D. Gonin and C. Noël, Liquid Crystalline Polymers, in Organic Thin Films for Waveguiding Nonlinear Optics, F. Kajzar and J. Swalen Eds, Gordon & Breach Sc. Publ., Amsterdam1996, pp.221–288.

Okada-Shudo, Y.

F. Kajzar, Y. Okada-Shudo, C. Meritt, and Z. Kafafi, “Second- and third-order non-linear optical properties of multilayered structures and composites of C60 with electron donors,” Synth. Met. 117, 189–193 (2001).
[Crossref]

Ostroverkhov, V.

V. Ostroverkhov, R.G. Petschek, K.D. Singer, and R.J. Twieg, “Lambda-Shaped Chromophores for Chiral Nonlinear Optical Materials,” Chem. Phys. Lett. 340, 109–115 (2001).
[Crossref]

Ostroverkhov, Victor

Victor Ostroverkhov, Kenneth D. Singer, and Rolfe G. Petschek, “Second-order nonlinear optical processes in non-polar chiral materials: relationship between molecular and macroscopic properties,” J. Opt. Soc. Am B. 18, 1858–1865 (2001).
[Crossref]

Oudar, J. L.

J. L. Oudar and D. S. Chemla, “Hyperpolarizabilities of nitroanilines and their relations to the excited state dipole moment,” J. Chem. Phys 66, 2664–2667 (1977).
[Crossref]

Pagani, G. A.

A. Facchetti, E. Annoni, L. Beverina, L. Beverina, M. Morone, P. Zhu, T. J. Marks, and G. A. Pagani, ”Very large electro-optic responses in H-bonded heteroaromatic films grown by physical vapour deposition”, Nat. Mater. 3, 910–917 (2004).
[Crossref] [PubMed]

Petschek, R.G.

V. Ostroverkhov, R.G. Petschek, K.D. Singer, and R.J. Twieg, “Lambda-Shaped Chromophores for Chiral Nonlinear Optical Materials,” Chem. Phys. Lett. 340, 109–115 (2001).
[Crossref]

Petschek, Rolfe G.

Victor Ostroverkhov, Kenneth D. Singer, and Rolfe G. Petschek, “Second-order nonlinear optical processes in non-polar chiral materials: relationship between molecular and macroscopic properties,” J. Opt. Soc. Am B. 18, 1858–1865 (2001).
[Crossref]

Petty, M. C.

M. C. Petty, Langmuir-Blodgett Films, An Introduction, Cambridge University Press, Cambridge1996.

Pisignano, Dario

Marco Mazzeo, Vincenzo Vitale, Fabio Della Sala, Dario Pisignano, Marco Anni, Giovanna Barbarella, Laura Favaretto, Alberto Zanelli, Roberto Cingolani, and Giuseppe Gigli, “New branched thiophene-based oligomers for bright organic light emitting devices,” Adv. Mater. 15, 2060–2063 (2003).
[Crossref]

Sala, Fabio Della

Marco Mazzeo, Vincenzo Vitale, Fabio Della Sala, Dario Pisignano, Marco Anni, Giovanna Barbarella, Laura Favaretto, Alberto Zanelli, Roberto Cingolani, and Giuseppe Gigli, “New branched thiophene-based oligomers for bright organic light emitting devices,” Adv. Mater. 15, 2060–2063 (2003).
[Crossref]

Singer, K. D.

K. D. Singer, J. E. Sohn, and S. J. Lalama, Second harmonic generation in poled polymer films, Appl. Phys. Lett. 49, 248 (1986)
[Crossref]

Singer, K.D.

V. Ostroverkhov, R.G. Petschek, K.D. Singer, and R.J. Twieg, “Lambda-Shaped Chromophores for Chiral Nonlinear Optical Materials,” Chem. Phys. Lett. 340, 109–115 (2001).
[Crossref]

Singer, Kenneth D.

Victor Ostroverkhov, Kenneth D. Singer, and Rolfe G. Petschek, “Second-order nonlinear optical processes in non-polar chiral materials: relationship between molecular and macroscopic properties,” J. Opt. Soc. Am B. 18, 1858–1865 (2001).
[Crossref]

Sohn, J. E.

K. D. Singer, J. E. Sohn, and S. J. Lalama, Second harmonic generation in poled polymer films, Appl. Phys. Lett. 49, 248 (1986)
[Crossref]

Swalen, J.

J. Swalen and F. Kajzar, Introduction, in Organic Thin Films for Waveguiding Nonlinear Optics, F. Kajzar and J. Swalen Eds, Gordon & Breach Sc. Publ., Amsterdam1996, pp. 1–85

Tang, Q.

Ch. Bosshard, M. Küpfer, M. Flörsheimer, Th. Borer, P. Günter, Q. Tang, and S. Zahir, “Investigation of chromophore orientation of 2-docosylamino-5-nitropyridine and derivatives by nonlinear optical techniques,” Thin Solid Films 210/211, 198–201 (1992)]
[Crossref]

Twieg, R.J.

V. Ostroverkhov, R.G. Petschek, K.D. Singer, and R.J. Twieg, “Lambda-Shaped Chromophores for Chiral Nonlinear Optical Materials,” Chem. Phys. Lett. 340, 109–115 (2001).
[Crossref]

C.R Moylan, S Ermer, S.M. Lovejoy, I.-H. McComb, D.S. Leung, R. Wortmann, P. Krdmer, and R.J. Twieg, “Dicyanomethylene)pyran derivatives with C2v symmetry: An unusual class of nonlinear optical chromophores.” JACS 118, 12950–12955 (1996)
[Crossref]

Vitale, Vincenzo

Marco Mazzeo, Vincenzo Vitale, Fabio Della Sala, Dario Pisignano, Marco Anni, Giovanna Barbarella, Laura Favaretto, Alberto Zanelli, Roberto Cingolani, and Giuseppe Gigli, “New branched thiophene-based oligomers for bright organic light emitting devices,” Adv. Mater. 15, 2060–2063 (2003).
[Crossref]

Watanabe, T.

T. Watanabe, H. Yamammoto, T. Hosomin, and S. Miyata, in Organic Molecules for Nonlinear Optics and Photonics, J. Messier, F. Kajzar, and P. Prasad, Eds, Kluwer Acad. Publ., Dordrecht (1991).

Wortmann, R.

C.R Moylan, S Ermer, S.M. Lovejoy, I.-H. McComb, D.S. Leung, R. Wortmann, P. Krdmer, and R.J. Twieg, “Dicyanomethylene)pyran derivatives with C2v symmetry: An unusual class of nonlinear optical chromophores.” JACS 118, 12950–12955 (1996)
[Crossref]

Yamammoto, H.

T. Watanabe, H. Yamammoto, T. Hosomin, and S. Miyata, in Organic Molecules for Nonlinear Optics and Photonics, J. Messier, F. Kajzar, and P. Prasad, Eds, Kluwer Acad. Publ., Dordrecht (1991).

Zahir, S.

Ch. Bosshard, M. Küpfer, M. Flörsheimer, Th. Borer, P. Günter, Q. Tang, and S. Zahir, “Investigation of chromophore orientation of 2-docosylamino-5-nitropyridine and derivatives by nonlinear optical techniques,” Thin Solid Films 210/211, 198–201 (1992)]
[Crossref]

Zanelli, Alberto

Giovanna Barbarella, Laura Favaretto, Alberto Zanelli, Giuseppe Gigli, Marco Mazzeo, Marco Anni, and Alessandro Bongini, “V-shaped thiophene based oligomers with improved electroluminescence properties,” Adv. Funct. Mater. 15, 664–670 (2005).
[Crossref]

Marco Mazzeo, Vincenzo Vitale, Fabio Della Sala, Dario Pisignano, Marco Anni, Giovanna Barbarella, Laura Favaretto, Alberto Zanelli, Roberto Cingolani, and Giuseppe Gigli, “New branched thiophene-based oligomers for bright organic light emitting devices,” Adv. Mater. 15, 2060–2063 (2003).
[Crossref]

Zhu, P.

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Figures (5)

Fig. 1.
Fig. 1.

Left: Molecular structure of 2,3-Bis-(2,2’bithiophen-5-yl)-benzo[b]thiophene1,1-dioxide (V-BT1) and (right) of 2,3-Bis-(3,3’-dicyclohexyl-[2,2’]bithiophenyl-5-yl)-benzo[b]thiophene1,1-dioxide (V-BT2).

Fig. 2.
Fig. 2.

One-photon absorption spectra of 2,3-Bis-(2,2’bithiophen-5-yl)-benzo[b]thiophene1,1-dioxide (V-BT1, red-circles) and of 2,3-Bis-(3,3’-dicyclohexyl-[2,2’]bithiophenyl-5-yl)-benzo[b]thiophene1,1-dioxide (V-BT2, blue-line) thin films. The films are vacuum deposited and are 80nm thick. The vertical line marks the expected SHG signal.

Fig. 3.
Fig. 3.

Incidence angle dependence of SHG intensity for V-BT2 thin film at different fundamental harmonic beam polarization configurations.

Fig. 4.
Fig. 4.

The variation of χ (2)xxz (oe-17-04-2557-i001) and χ (2)zzz (oe-17-04-2557-i002) versus the films thickness for films of 2,3-Bis-(3,3’-dicyclohexyl-[2,2’]bithiophenyl-5-yl)-benzo[b]thiophene1,1-dioxide (V-BT2). The data are affected by a 10% error bar.

Fig. 5.
Fig. 5.

Reference frame used for studied thin films.

Tables (1)

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Table 1. Second order NLO susceptibilities of studied molecules thin films, made by vacuum sublimation technique.

Equations (4)

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I 2 ω s p P sp ( ω , 2 ω , θ ω s , θ ω s , χ XXZ ( 2 ) ) 2 I ω 2
P sp ( ω , 2 ω , θ ω s , θ ω s , χ sp ( 2 ) ) = χ XXZ ( 2 ) sin 2 θ ω s cos θ 2 ω s
I 2 ω p p P pp ( ω , 2 ω , θ ω p , θ ω p , χ XXZ ( 2 ) , χ ZZZ ( 2 ) ) 2 I ω 2
P pp ( ω , 2 ω , θ ω s , θ ω s , χ XX Z ( 2 ) , χ ZZZ ( 2 ) ) = χ ZZZ ( 2 ) sin 2 θ ω p sin θ 2 ω p + χ XX Z ( 2 ) cos θ ω p ( cos θ ω p + 2 sin θ ω p cos θ 2 ω p )

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