Synthesis and properties of 7,10-dithiafluoroanthenes and their 8,9-dihydro derivatives with chalcogen substituents

Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals

Volumn 296, Issue , 1997, Pages 19-30

  Tani, Hiroyuki ^a   Kawada, Yoshihiro ^a   Azuma, Nagao ^a   Ono, Noboru ^a  

^a EHIME UNIVERSITY   (Japan)

Author keywords

Charge transfer complex; Electrical conductivity; Organic donor; Radical cation salt; X ray crystallographic analysis

Indexed keywords

CHARGE TRANSFER; CRYSTALLIZATION; ELECTRIC CONDUCTIVITY OF SOLIDS; LIQUID CRYSTALS; MOLECULAR CRYSTALS; ORGANIC CONDUCTORS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); VAN DER WAALS FORCES; X RAY CRYSTALLOGRAPHY;

CHALCOGEN SUBSTITUENTS; ORGANIC DONORS; RADICAL CATION SALTS;

AROMATIC COMPOUNDS;

EID: 0031369971     PISSN: 1058725X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

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22. K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Chem. Lett., 551 (1986); H. Miyamoto, K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Tetrahedron Lett., 27, 2011 (1986); T. Otsubo, N. Sukenobe, Y. Aso, and F. Ogura, Chem. Lett., 315 (1987); T. Otsubo, H. Miyamoto, Y. Aso, and F. Ogura, Synth. Met., 19, 595 (1987); K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 61, 953 (1988); Y. Aso, K. Yui, T. Miyoshi, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 61, 2013 (1988); T. Otsubo, N. Sukenobe, Y. Aso, and F. Ogura, Synth. Met., 27, B509 (1988); K. Takimiya, H. Miyamoto, Y. Aso, T. Otsubo, and F. Ogura, Chem Lett., 567 (1990); H. Miyamoto, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 63, 2441 (1990); H. Miyamoto, K. Takimiya, Y. Aso, T. Otsubo, and F. Ogura, Synth. Met., 42, 2389 (1991); K. Takimiya, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 64, 2091 (1991); K. Takimiya, A. Ohnishi, Y. Aso, T. Otsubo, and F. Ogura, J. Chem. Soc., Chem. Commun., 278 (1992); F. Ogura, T. Otsubo, and Y. Aso, Pure Appl. Chem., 65, 683 (1993); K. Takimiya, A. Ohnishi, Y. Aso, T. Otsubo, F. Ogura, K. Kawabata, K. Tanaka, and M. Mizutani, Bull. Chem. Soc. Jpn., 67, 766 (1994); K. Takimiya, Y. Shibata, A. Ohnishi, Y. Aso, T. Otsubo, and F. Ogura, J. Mater. Chem., 5, 1539 (1995).
23. K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Chem. Lett., 551 (1986); H. Miyamoto, K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Tetrahedron Lett., 27, 2011 (1986); T. Otsubo, N. Sukenobe, Y. Aso, and F. Ogura, Chem. Lett., 315 (1987); T. Otsubo, H. Miyamoto, Y. Aso, and F. Ogura, Synth. Met., 19, 595 (1987); K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 61, 953 (1988); Y. Aso, K. Yui, T. Miyoshi, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 61, 2013 (1988); T. Otsubo, N. Sukenobe, Y. Aso, and F. Ogura, Synth. Met., 27, B509 (1988); K. Takimiya, H. Miyamoto, Y. Aso, T. Otsubo, and F. Ogura, Chem Lett., 567 (1990); H. Miyamoto, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 63, 2441 (1990); H. Miyamoto, K. Takimiya, Y. Aso, T. Otsubo, and F. Ogura, Synth. Met., 42, 2389 (1991); K. Takimiya, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 64, 2091 (1991); K. Takimiya, A. Ohnishi, Y. Aso, T. Otsubo, and F. Ogura, J. Chem. Soc., Chem. Commun., 278 (1992); F. Ogura, T. Otsubo, and Y. Aso, Pure Appl. Chem., 65, 683 (1993); K. Takimiya, A. Ohnishi, Y. Aso, T. Otsubo, F. Ogura, K. Kawabata, K. Tanaka, and M. Mizutani, Bull. Chem. Soc. Jpn., 67, 766 (1994); K. Takimiya, Y. Shibata, A. Ohnishi, Y. Aso, T. Otsubo, and F. Ogura, J. Mater. Chem., 5, 1539 (1995).
24. K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Chem. Lett., 551 (1986); H. Miyamoto, K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Tetrahedron Lett., 27, 2011 (1986); T. Otsubo, N. Sukenobe, Y. Aso, and F. Ogura, Chem. Lett., 315 (1987); T. Otsubo, H. Miyamoto, Y. Aso, and F. Ogura, Synth. Met., 19, 595 (1987); K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 61, 953 (1988); Y. Aso, K. Yui, T. Miyoshi, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 61, 2013 (1988); T. Otsubo, N. Sukenobe, Y. Aso, and F. Ogura, Synth. Met., 27, B509 (1988); K. Takimiya, H. Miyamoto, Y. Aso, T. Otsubo, and F. Ogura, Chem Lett., 567 (1990); H. Miyamoto, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 63, 2441 (1990); H. Miyamoto, K. Takimiya, Y. Aso, T. Otsubo, and F. Ogura, Synth. Met., 42, 2389 (1991); K. Takimiya, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 64, 2091 (1991); K. Takimiya, A. Ohnishi, Y. Aso, T. Otsubo, and F. Ogura, J. Chem. Soc., Chem. Commun., 278 (1992); F. Ogura, T. Otsubo, and Y. Aso, Pure Appl. Chem., 65, 683 (1993); K. Takimiya, A. Ohnishi, Y. Aso, T. Otsubo, F. Ogura, K. Kawabata, K. Tanaka, and M. Mizutani, Bull. Chem. Soc. Jpn., 67, 766 (1994); K. Takimiya, Y. Shibata, A. Ohnishi, Y. Aso, T. Otsubo, and F. Ogura, J. Mater. Chem., 5, 1539 (1995).
25. K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Chem. Lett., 551 (1986); H. Miyamoto, K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Tetrahedron Lett., 27, 2011 (1986); T. Otsubo, N. Sukenobe, Y. Aso, and F. Ogura, Chem. Lett., 315 (1987); T. Otsubo, H. Miyamoto, Y. Aso, and F. Ogura, Synth. Met., 19, 595 (1987); K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 61, 953 (1988); Y. Aso, K. Yui, T. Miyoshi, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 61, 2013 (1988); T. Otsubo, N. Sukenobe, Y. Aso, and F. Ogura, Synth. Met., 27, B509 (1988); K. Takimiya, H. Miyamoto, Y. Aso, T. Otsubo, and F. Ogura, Chem Lett., 567 (1990); H. Miyamoto, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 63, 2441 (1990); H. Miyamoto, K. Takimiya, Y. Aso, T. Otsubo, and F. Ogura, Synth. Met., 42, 2389 (1991); K. Takimiya, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 64, 2091 (1991); K. Takimiya, A. Ohnishi, Y. Aso, T. Otsubo, and F. Ogura, J. Chem. Soc., Chem. Commun., 278 (1992); F. Ogura, T. Otsubo, and Y. Aso, Pure Appl. Chem., 65, 683 (1993); K. Takimiya, A. Ohnishi, Y. Aso, T. Otsubo, F. Ogura, K. Kawabata, K. Tanaka, and M. Mizutani, Bull. Chem. Soc. Jpn., 67, 766 (1994); K. Takimiya, Y. Shibata, A. Ohnishi, Y. Aso, T. Otsubo, and F. Ogura, J. Mater. Chem., 5, 1539 (1995).
26. K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Chem. Lett., 551 (1986); H. Miyamoto, K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Tetrahedron Lett., 27, 2011 (1986); T. Otsubo, N. Sukenobe, Y. Aso, and F. Ogura, Chem. Lett., 315 (1987); T. Otsubo, H. Miyamoto, Y. Aso, and F. Ogura, Synth. Met., 19, 595 (1987); K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 61, 953 (1988); Y. Aso, K. Yui, T. Miyoshi, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 61, 2013 (1988); T. Otsubo, N. Sukenobe, Y. Aso, and F. Ogura, Synth. Met., 27, B509 (1988); K. Takimiya, H. Miyamoto, Y. Aso, T. Otsubo, and F. Ogura, Chem Lett., 567 (1990); H. Miyamoto, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 63, 2441 (1990); H. Miyamoto, K. Takimiya, Y. Aso, T. Otsubo, and F. Ogura, Synth. Met., 42, 2389 (1991); K. Takimiya, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 64, 2091 (1991); K. Takimiya, A. Ohnishi, Y. Aso, T. Otsubo, and F. Ogura, J. Chem. Soc., Chem. Commun., 278 (1992); F. Ogura, T. Otsubo, and Y. Aso, Pure Appl. Chem., 65, 683 (1993); K. Takimiya, A. Ohnishi, Y. Aso, T. Otsubo, F. Ogura, K. Kawabata, K. Tanaka, and M. Mizutani, Bull. Chem. Soc. Jpn., 67, 766 (1994); K. Takimiya, Y. Shibata, A. Ohnishi, Y. Aso, T. Otsubo, and F. Ogura, J. Mater. Chem., 5, 1539 (1995).
27. K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Chem. Lett., 551 (1986); H. Miyamoto, K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Tetrahedron Lett., 27, 2011 (1986); T. Otsubo, N. Sukenobe, Y. Aso, and F. Ogura, Chem. Lett., 315 (1987); T. Otsubo, H. Miyamoto, Y. Aso, and F. Ogura, Synth. Met., 19, 595 (1987); K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 61, 953 (1988); Y. Aso, K. Yui, T. Miyoshi, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 61, 2013 (1988); T. Otsubo, N. Sukenobe, Y. Aso, and F. Ogura, Synth. Met., 27, B509 (1988); K. Takimiya, H. Miyamoto, Y. Aso, T. Otsubo, and F. Ogura, Chem Lett., 567 (1990); H. Miyamoto, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 63, 2441 (1990); H. Miyamoto, K. Takimiya, Y. Aso, T. Otsubo, and F. Ogura, Synth. Met., 42, 2389 (1991); K. Takimiya, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 64, 2091 (1991); K. Takimiya, A. Ohnishi, Y. Aso, T. Otsubo, and F. Ogura, J. Chem. Soc., Chem. Commun., 278 (1992); F. Ogura, T. Otsubo, and Y. Aso, Pure Appl. Chem., 65, 683 (1993); K. Takimiya, A. Ohnishi, Y. Aso, T. Otsubo, F. Ogura, K. Kawabata, K. Tanaka, and M. Mizutani, Bull. Chem. Soc. Jpn., 67, 766 (1994); K. Takimiya, Y. Shibata, A. Ohnishi, Y. Aso, T. Otsubo, and F. Ogura, J. Mater. Chem., 5, 1539 (1995).
28. K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Chem. Lett., 551 (1986); H. Miyamoto, K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Tetrahedron Lett., 27, 2011 (1986); T. Otsubo, N. Sukenobe, Y. Aso, and F. Ogura, Chem. Lett., 315 (1987); T. Otsubo, H. Miyamoto, Y. Aso, and F. Ogura, Synth. Met., 19, 595 (1987); K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 61, 953 (1988); Y. Aso, K. Yui, T. Miyoshi, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 61, 2013 (1988); T. Otsubo, N. Sukenobe, Y. Aso, and F. Ogura, Synth. Met., 27, B509 (1988); K. Takimiya, H. Miyamoto, Y. Aso, T. Otsubo, and F. Ogura, Chem Lett., 567 (1990); H. Miyamoto, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 63, 2441 (1990); H. Miyamoto, K. Takimiya, Y. Aso, T. Otsubo, and F. Ogura, Synth. Met., 42, 2389 (1991); K. Takimiya, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 64, 2091 (1991); K. Takimiya, A. Ohnishi, Y. Aso, T. Otsubo, and F. Ogura, J. Chem. Soc., Chem. Commun., 278 (1992); F. Ogura, T. Otsubo, and Y. Aso, Pure Appl. Chem., 65, 683 (1993); K. Takimiya, A. Ohnishi, Y. Aso, T. Otsubo, F. Ogura, K. Kawabata, K. Tanaka, and M. Mizutani, Bull. Chem. Soc. Jpn., 67, 766 (1994); K. Takimiya, Y. Shibata, A. Ohnishi, Y. Aso, T. Otsubo, and F. Ogura, J. Mater. Chem., 5, 1539 (1995).
29. K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Chem. Lett., 551 (1986); H. Miyamoto, K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Tetrahedron Lett., 27, 2011 (1986); T. Otsubo, N. Sukenobe, Y. Aso, and F. Ogura, Chem. Lett., 315 (1987); T. Otsubo, H. Miyamoto, Y. Aso, and F. Ogura, Synth. Met., 19, 595 (1987); K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 61, 953 (1988); Y. Aso, K. Yui, T. Miyoshi, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 61, 2013 (1988); T. Otsubo, N. Sukenobe, Y. Aso, and F. Ogura, Synth. Met., 27, B509 (1988); K. Takimiya, H. Miyamoto, Y. Aso, T. Otsubo, and F. Ogura, Chem Lett., 567 (1990); H. Miyamoto, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 63, 2441 (1990); H. Miyamoto, K. Takimiya, Y. Aso, T. Otsubo, and F. Ogura, Synth. Met., 42, 2389 (1991); K. Takimiya, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 64, 2091 (1991); K. Takimiya, A. Ohnishi, Y. Aso, T. Otsubo, and F. Ogura, J. Chem. Soc., Chem. Commun., 278 (1992); F. Ogura, T. Otsubo, and Y. Aso, Pure Appl. Chem., 65, 683 (1993); K. Takimiya, A. Ohnishi, Y. Aso, T. Otsubo, F. Ogura, K. Kawabata, K. Tanaka, and M. Mizutani, Bull. Chem. Soc. Jpn., 67, 766 (1994); K. Takimiya, Y. Shibata, A. Ohnishi, Y. Aso, T. Otsubo, and F. Ogura, J. Mater. Chem., 5, 1539 (1995).
30. K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Chem. Lett., 551 (1986); H. Miyamoto, K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Tetrahedron Lett., 27, 2011 (1986); T. Otsubo, N. Sukenobe, Y. Aso, and F. Ogura, Chem. Lett., 315 (1987); T. Otsubo, H. Miyamoto, Y. Aso, and F. Ogura, Synth. Met., 19, 595 (1987); K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 61, 953 (1988); Y. Aso, K. Yui, T. Miyoshi, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 61, 2013 (1988); T. Otsubo, N. Sukenobe, Y. Aso, and F. Ogura, Synth. Met., 27, B509 (1988); K. Takimiya, H. Miyamoto, Y. Aso, T. Otsubo, and F. Ogura, Chem Lett., 567 (1990); H. Miyamoto, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 63, 2441 (1990); H. Miyamoto, K. Takimiya, Y. Aso, T. Otsubo, and F. Ogura, Synth. Met., 42, 2389 (1991); K. Takimiya, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 64, 2091 (1991); K. Takimiya, A. Ohnishi, Y. Aso, T. Otsubo, and F. Ogura, J. Chem. Soc., Chem. Commun., 278 (1992); F. Ogura, T. Otsubo, and Y. Aso, Pure Appl. Chem., 65, 683 (1993); K. Takimiya, A. Ohnishi, Y. Aso, T. Otsubo, F. Ogura, K. Kawabata, K. Tanaka, and M. Mizutani, Bull. Chem. Soc. Jpn., 67, 766 (1994); K. Takimiya, Y. Shibata, A. Ohnishi, Y. Aso, T. Otsubo, and F. Ogura, J. Mater. Chem., 5, 1539 (1995).
31. K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Chem. Lett., 551 (1986); H. Miyamoto, K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Tetrahedron Lett., 27, 2011 (1986); T. Otsubo, N. Sukenobe, Y. Aso, and F. Ogura, Chem. Lett., 315 (1987); T. Otsubo, H. Miyamoto, Y. Aso, and F. Ogura, Synth. Met., 19, 595 (1987); K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 61, 953 (1988); Y. Aso, K. Yui, T. Miyoshi, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 61, 2013 (1988); T. Otsubo, N. Sukenobe, Y. Aso, and F. Ogura, Synth. Met., 27, B509 (1988); K. Takimiya, H. Miyamoto, Y. Aso, T. Otsubo, and F. Ogura, Chem Lett., 567 (1990); H. Miyamoto, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 63, 2441 (1990); H. Miyamoto, K. Takimiya, Y. Aso, T. Otsubo, and F. Ogura, Synth. Met., 42, 2389 (1991); K. Takimiya, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 64, 2091 (1991); K. Takimiya, A. Ohnishi, Y. Aso, T. Otsubo, and F. Ogura, J. Chem. Soc., Chem. Commun., 278 (1992); F. Ogura, T. Otsubo, and Y. Aso, Pure Appl. Chem., 65, 683 (1993); K. Takimiya, A. Ohnishi, Y. Aso, T. Otsubo, F. Ogura, K. Kawabata, K. Tanaka, and M. Mizutani, Bull. Chem. Soc. Jpn., 67, 766 (1994); K. Takimiya, Y. Shibata, A. Ohnishi, Y. Aso, T. Otsubo, and F. Ogura, J. Mater. Chem., 5, 1539 (1995).
32. K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Chem. Lett., 551 (1986); H. Miyamoto, K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Tetrahedron Lett., 27, 2011 (1986); T. Otsubo, N. Sukenobe, Y. Aso, and F. Ogura, Chem. Lett., 315 (1987); T. Otsubo, H. Miyamoto, Y. Aso, and F. Ogura, Synth. Met., 19, 595 (1987); K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 61, 953 (1988); Y. Aso, K. Yui, T. Miyoshi, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 61, 2013 (1988); T. Otsubo, N. Sukenobe, Y. Aso, and F. Ogura, Synth. Met., 27, B509 (1988); K. Takimiya, H. Miyamoto, Y. Aso, T. Otsubo, and F. Ogura, Chem Lett., 567 (1990); H. Miyamoto, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 63, 2441 (1990); H. Miyamoto, K. Takimiya, Y. Aso, T. Otsubo, and F. Ogura, Synth. Met., 42, 2389 (1991); K. Takimiya, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. Soc. Jpn., 64, 2091 (1991); K. Takimiya, A. Ohnishi, Y. Aso, T. Otsubo, and F. Ogura, J. Chem. Soc., Chem. Commun., 278 (1992); F. Ogura, T. Otsubo, and Y. Aso, Pure Appl. Chem., 65, 683 (1993); K. Takimiya, A. Ohnishi, Y. Aso, T. Otsubo, F. Ogura, K. Kawabata, K. Tanaka, and M. Mizutani, Bull. Chem. Soc. Jpn., 67, 766 (1994); K. Takimiya, Y. Shibata, A. Ohnishi, Y. Aso, T. Otsubo, and F. Ogura, J. Mater. Chem., 5, 1539 (1995).
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38. 4: C, 55.60; H, 2.00%.
39. -2). Black long needles grew on the anode.
40. 12 and took anomalous dispersion into account.
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