Novel organic crystals with red-violet metallic luster: 1-aryl-2-(2-thienyl)-5-[5-(tricyanoethenyl)-2-thienyl]pyrrole derivatives bearing a heteroatom combined methyl substituent

Tetrahedron

Volumn 58, Issue 51, 2002, Pages 10225-10231

  Zhao, Rui ^a   Akazome, Motohiro ^a   Matsumoto, Shoji ^a   Ogura, Katsuyuki ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

conjugated organic compound; Heteroatom combined methyl substituent; Intermolecular CN C C interaction; Red violet metallic luster; Ribbon like molecular arrangement

Indexed keywords

1,2 (2 THIENYL) 5 [5 (TRICYANOETHYL) 2 THIENYL]PYRROLE DERIVATIVE; HALOGEN; METHYL GROUP; ORGANIC COMPOUND; PHENYL GROUP; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; COLOR; CONJUGATION; CRYSTAL; CRYSTAL STRUCTURE; HYDROGEN BOND; MOLECULE; PRIORITY JOURNAL;

VIOLA (ANGIOSPERM);

EID: 18744385245     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01354-6     Document Type: Article

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19. For examples, see: (a) Breitung E.M., Shu C.-F., McMahon R.J. J. Am. Chem. Soc. 122:2000;1154 (b) Moore A.J., Chesney A., Bryce M.R., Batsanov A.S., Kelly J.F., Howard J.A.K., Perepichka I.F., Perepichka D.F., Meshulam G., Berkovic G., Kotler Z., Mazor R., Khodorkovsky V. Eur. J. Org. Chem. 2001;2671 (c) McCormac T., Farrell D. Electrochim. Acta. 46:2000;3287 (d) Robinson B.H., Dalton L.R., Harper A.W., Ren A., Wang F., Zhang C., Todorova G., Lee M., Aniszfeld R., Garner S., Chen A., Steier W.H., Houbrecht S., Persoons A., Ledoux I., Zyss J., Jen A.K.-Y. Chem. Phys. 245:1999;35 (e) Lambert C., Gaschler W., Schmalzlin E., Meerholz K., Brauchle C. J. Chem. Soc., Perkin Trans. 2. 1999;577 (f) Cai C., Liakatas I., Wong M.-S., Bösch M., Bosshard C., Günter P., Concilio S., Tirelli N., Suter U.W. Org. Lett. 11:1999;1847 (g) Wang Y.-K., Shu C.-F., Breitung E.M., McMahon R.J. J. Mater. Chem. 9:1999;1449 (h) Bu X.R., Li H., Derveer D.V., Mintz E.A. Tetrahedron Lett. 37:1996;7331 (i) Jen A.K.-Y., Rao V.P., Drost K.J., Wong K.Y., Cava M.P. J. Chem. Soc., Chem. Commun. 1994;2057 (j) Rao V.P., Jen A.K.-Y., Wong K.Y., Drost K.J. J. Chem. Soc., Chem. Commun. 1993;1118.
20. For examples, see: (a) Breitung E.M., Shu C.-F., McMahon R.J. J. Am. Chem. Soc. 122:2000;1154 (b) Moore A.J., Chesney A., Bryce M.R., Batsanov A.S., Kelly J.F., Howard J.A.K., Perepichka I.F., Perepichka D.F., Meshulam G., Berkovic G., Kotler Z., Mazor R., Khodorkovsky V. Eur. J. Org. Chem. 2001;2671 (c) McCormac T., Farrell D. Electrochim. Acta. 46:2000;3287 (d) Robinson B.H., Dalton L.R., Harper A.W., Ren A., Wang F., Zhang C., Todorova G., Lee M., Aniszfeld R., Garner S., Chen A., Steier W.H., Houbrecht S., Persoons A., Ledoux I., Zyss J., Jen A.K.-Y. Chem. Phys. 245:1999;35 (e) Lambert C., Gaschler W., Schmalzlin E., Meerholz K., Brauchle C. J. Chem. Soc., Perkin Trans. 2. 1999;577 (f) Cai C., Liakatas I., Wong M.-S., Bösch M., Bosshard C., Günter P., Concilio S., Tirelli N., Suter U.W. Org. Lett. 11:1999;1847 (g) Wang Y.-K., Shu C.-F., Breitung E.M., McMahon R.J. J. Mater. Chem. 9:1999;1449 (h) Bu X.R., Li H., Derveer D.V., Mintz E.A. Tetrahedron Lett. 37:1996;7331 (i) Jen A.K.-Y., Rao V.P., Drost K.J., Wong K.Y., Cava M.P. J. Chem. Soc., Chem. Commun. 1994;2057 (j) Rao V.P., Jen A.K.-Y., Wong K.Y., Drost K.J. J. Chem. Soc., Chem. Commun. 1993;1118.
21. For examples, see: (a) Breitung E.M., Shu C.-F., McMahon R.J. J. Am. Chem. Soc. 122:2000;1154 (b) Moore A.J., Chesney A., Bryce M.R., Batsanov A.S., Kelly J.F., Howard J.A.K., Perepichka I.F., Perepichka D.F., Meshulam G., Berkovic G., Kotler Z., Mazor R., Khodorkovsky V. Eur. J. Org. Chem. 2001;2671 (c) McCormac T., Farrell D. Electrochim. Acta. 46:2000;3287 (d) Robinson B.H., Dalton L.R., Harper A.W., Ren A., Wang F., Zhang C., Todorova G., Lee M., Aniszfeld R., Garner S., Chen A., Steier W.H., Houbrecht S., Persoons A., Ledoux I., Zyss J., Jen A.K.-Y. Chem. Phys. 245:1999;35 (e) Lambert C., Gaschler W., Schmalzlin E., Meerholz K., Brauchle C. J. Chem. Soc., Perkin Trans. 2. 1999;577 (f) Cai C., Liakatas I., Wong M.-S., Bösch M., Bosshard C., Günter P., Concilio S., Tirelli N., Suter U.W. Org. Lett. 11:1999;1847 (g) Wang Y.-K., Shu C.-F., Breitung E.M., McMahon R.J. J. Mater. Chem. 9:1999;1449 (h) Bu X.R., Li H., Derveer D.V., Mintz E.A. Tetrahedron Lett. 37:1996;7331 (i) Jen A.K.-Y., Rao V.P., Drost K.J., Wong K.Y., Cava M.P. J. Chem. Soc., Chem. Commun. 1994;2057 (j) Rao V.P., Jen A.K.-Y., Wong K.Y., Drost K.J. J. Chem. Soc., Chem. Commun. 1993;1118.
22. For examples, see: (a) Breitung E.M., Shu C.-F., McMahon R.J. J. Am. Chem. Soc. 122:2000;1154 (b) Moore A.J., Chesney A., Bryce M.R., Batsanov A.S., Kelly J.F., Howard J.A.K., Perepichka I.F., Perepichka D.F., Meshulam G., Berkovic G., Kotler Z., Mazor R., Khodorkovsky V. Eur. J. Org. Chem. 2001;2671 (c) McCormac T., Farrell D. Electrochim. Acta. 46:2000;3287 (d) Robinson B.H., Dalton L.R., Harper A.W., Ren A., Wang F., Zhang C., Todorova G., Lee M., Aniszfeld R., Garner S., Chen A., Steier W.H., Houbrecht S., Persoons A., Ledoux I., Zyss J., Jen A.K.-Y. Chem. Phys. 245:1999;35 (e) Lambert C., Gaschler W., Schmalzlin E., Meerholz K., Brauchle C. J. Chem. Soc., Perkin Trans. 2. 1999;577 (f) Cai C., Liakatas I., Wong M.-S., Bösch M., Bosshard C., Günter P., Concilio S., Tirelli N., Suter U.W. Org. Lett. 11:1999;1847 (g) Wang Y.-K., Shu C.-F., Breitung E.M., McMahon R.J. J. Mater. Chem. 9:1999;1449 (h) Bu X.R., Li H., Derveer D.V., Mintz E.A. Tetrahedron Lett. 37:1996;7331 (i) Jen A.K.-Y., Rao V.P., Drost K.J., Wong K.Y., Cava M.P. J. Chem. Soc., Chem. Commun. 1994;2057 (j) Rao V.P., Jen A.K.-Y., Wong K.Y., Drost K.J. J. Chem. Soc., Chem. Commun. 1993;1118.
23. For examples, see: (a) Breitung E.M., Shu C.-F., McMahon R.J. J. Am. Chem. Soc. 122:2000;1154 (b) Moore A.J., Chesney A., Bryce M.R., Batsanov A.S., Kelly J.F., Howard J.A.K., Perepichka I.F., Perepichka D.F., Meshulam G., Berkovic G., Kotler Z., Mazor R., Khodorkovsky V. Eur. J. Org. Chem. 2001;2671 (c) McCormac T., Farrell D. Electrochim. Acta. 46:2000;3287 (d) Robinson B.H., Dalton L.R., Harper A.W., Ren A., Wang F., Zhang C., Todorova G., Lee M., Aniszfeld R., Garner S., Chen A., Steier W.H., Houbrecht S., Persoons A., Ledoux I., Zyss J., Jen A.K.-Y. Chem. Phys. 245:1999;35 (e) Lambert C., Gaschler W., Schmalzlin E., Meerholz K., Brauchle C. J. Chem. Soc., Perkin Trans. 2. 1999;577 (f) Cai C., Liakatas I., Wong M.-S., Bösch M., Bosshard C., Günter P., Concilio S., Tirelli N., Suter U.W. Org. Lett. 11:1999;1847 (g) Wang Y.-K., Shu C.-F., Breitung E.M., McMahon R.J. J. Mater. Chem. 9:1999;1449 (h) Bu X.R., Li H., Derveer D.V., Mintz E.A. Tetrahedron Lett. 37:1996;7331 (i) Jen A.K.-Y., Rao V.P., Drost K.J., Wong K.Y., Cava M.P. J. Chem. Soc., Chem. Commun. 1994;2057 (j) Rao V.P., Jen A.K.-Y., Wong K.Y., Drost K.J. J. Chem. Soc., Chem. Commun. 1993;1118.
24. For examples, see: (a) Breitung E.M., Shu C.-F., McMahon R.J. J. Am. Chem. Soc. 122:2000;1154 (b) Moore A.J., Chesney A., Bryce M.R., Batsanov A.S., Kelly J.F., Howard J.A.K., Perepichka I.F., Perepichka D.F., Meshulam G., Berkovic G., Kotler Z., Mazor R., Khodorkovsky V. Eur. J. Org. Chem. 2001;2671 (c) McCormac T., Farrell D. Electrochim. Acta. 46:2000;3287 (d) Robinson B.H., Dalton L.R., Harper A.W., Ren A., Wang F., Zhang C., Todorova G., Lee M., Aniszfeld R., Garner S., Chen A., Steier W.H., Houbrecht S., Persoons A., Ledoux I., Zyss J., Jen A.K.-Y. Chem. Phys. 245:1999;35 (e) Lambert C., Gaschler W., Schmalzlin E., Meerholz K., Brauchle C. J. Chem. Soc., Perkin Trans. 2. 1999;577 (f) Cai C., Liakatas I., Wong M.-S., Bösch M., Bosshard C., Günter P., Concilio S., Tirelli N., Suter U.W. Org. Lett. 11:1999;1847 (g) Wang Y.-K., Shu C.-F., Breitung E.M., McMahon R.J. J. Mater. Chem. 9:1999;1449 (h) Bu X.R., Li H., Derveer D.V., Mintz E.A. Tetrahedron Lett. 37:1996;7331 (i) Jen A.K.-Y., Rao V.P., Drost K.J., Wong K.Y., Cava M.P. J. Chem. Soc., Chem. Commun. 1994;2057 (j) Rao V.P., Jen A.K.-Y., Wong K.Y., Drost K.J. J. Chem. Soc., Chem. Commun. 1993;1118.
25. For examples, see: (a) Breitung E.M., Shu C.-F., McMahon R.J. J. Am. Chem. Soc. 122:2000;1154 (b) Moore A.J., Chesney A., Bryce M.R., Batsanov A.S., Kelly J.F., Howard J.A.K., Perepichka I.F., Perepichka D.F., Meshulam G., Berkovic G., Kotler Z., Mazor R., Khodorkovsky V. Eur. J. Org. Chem. 2001;2671 (c) McCormac T., Farrell D. Electrochim. Acta. 46:2000;3287 (d) Robinson B.H., Dalton L.R., Harper A.W., Ren A., Wang F., Zhang C., Todorova G., Lee M., Aniszfeld R., Garner S., Chen A., Steier W.H., Houbrecht S., Persoons A., Ledoux I., Zyss J., Jen A.K.-Y. Chem. Phys. 245:1999;35 (e) Lambert C., Gaschler W., Schmalzlin E., Meerholz K., Brauchle C. J. Chem. Soc., Perkin Trans. 2. 1999;577 (f) Cai C., Liakatas I., Wong M.-S., Bösch M., Bosshard C., Günter P., Concilio S., Tirelli N., Suter U.W. Org. Lett. 11:1999;1847 (g) Wang Y.-K., Shu C.-F., Breitung E.M., McMahon R.J. J. Mater. Chem. 9:1999;1449 (h) Bu X.R., Li H., Derveer D.V., Mintz E.A. Tetrahedron Lett. 37:1996;7331 (i) Jen A.K.-Y., Rao V.P., Drost K.J., Wong K.Y., Cava M.P. J. Chem. Soc., Chem. Commun. 1994;2057 (j) Rao V.P., Jen A.K.-Y., Wong K.Y., Drost K.J. J. Chem. Soc., Chem. Commun. 1993;1118.
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