Design of Organic Solids pp 163-208

Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 198)

Crystalline Polymorphism of Organic Compounds

  • Caira Mino R. 
Chapter

Abstract

Crystal polymorphism is encountered in all areas of research involving solid substances. Its occurrence introduces complications during manufacturing processes and adds another dimension to the complexity of designing materials with specific properties. Research on polymorphism is fraught with unique difficulties due to the subtlety of polymorphic transformations and the inadvertent formation of pseudopolymorphs. In this report, a summary of thermodynamic, kinetic and structural considerations of polymorphism is presented. A wide variety of techniques appropriate to the study of organic crystalline polymorphism and pseu-dopolymorphism is then surveyed, ranging from simple crystal density measurement to observation of polymorphic transformations using variable-temperature synchrotron X-ray diffraction methods. Application of newer methodology described in this report is yielding fresh insights into the nature of the crystallization process, holding promise for a deeper understanding of the phenomenon of polymorphism and its practical control.

Keywords

Crystal polymorphism Pseudopolymorphism Crystallization 

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References

  1. 1.
    Mitscherlich E (1822) Ann Chim Phys 19:350Google Scholar
  2. 2.
    Dunitz JD (1996) In: Desiraju GR (ed) The crystal as a supramolecular entity: perspectives in supramolecular chemistry, vol 2. Wiley, New York, p 2Google Scholar
  3. 3.
    Desiraju GR (1989) Crystal engineering. Elsevier, AmsterdamGoogle Scholar
  4. 4.
    Sato K (1993) J Phys D: Appl Phys 26:B77CrossRefGoogle Scholar
  5. 5.
    Dunitz JD, Bernstein J (1995) Acc Chem Res 28:193CrossRefGoogle Scholar
  6. 6.
    Herbstein FH (1996) J Mol Struct 374:111CrossRefGoogle Scholar
  7. 7.
    Greenberg JH (1996) Mater Sci Eng R16:223Google Scholar
  8. 8.
    Bayard F, Decoret C, Royer J (1990) Stud Phys Theor Chem 69:211Google Scholar
  9. 9.
    Hernqvist L (1990) Food Struct 9:39Google Scholar
  10. 10.
    Kalman A, Argay G (1991) Kem Kozl 73:129Google Scholar
  11. 11.
    Bernstein J (1991) Polymorphism and the investigation of structure-property relations in organic solids. In: Garbarczyk JB, James DW (eds) Organic crystal chemistry. Oxford University Press, Oxford, chap 2Google Scholar
  12. 12.
    Cecchini MAG (1992) Publ. ACIESP 82:65Google Scholar
  13. 13.
    Bernstein J (1993) J Phys D: Appl Phys 26:B66CrossRefGoogle Scholar
  14. 14.
    Poole PH, Grande T, Sciortino F, Stanley HE, Angell CA (1995) Comput Mater Sci 4:373CrossRefGoogle Scholar
  15. 15.
    Lotz B (1995) Macromol Symp 94:97Google Scholar
  16. 16.
    Bernstein J, Davis RE, Shimoni L, Chang N-L (1995) Angew Chem Int Ed Engl 34:1555CrossRefGoogle Scholar
  17. 17.
    Wolff JJ (1996) Angew Chem Int Ed Engl 35:2195CrossRefGoogle Scholar
  18. 18.
    Ford JL, Timmins P (1989) Pharmaceutical thermal analysis, 1st edn. Ellis Horwood Limited, ChichesterGoogle Scholar
  19. 19.
    Byrn SR, Tobias B, Kessler D, Frye J, Sutton P, Saindon P, Kozlowski J (1989) Trans Am Crystallogr Assoc 24:41Google Scholar
  20. 20.
    Borka L, Haleblian JK (1990) Acta Pharm Jugosl 40:71Google Scholar
  21. 21.
    Borka L (1990) Spectroscopy (Eugene, Oreg) 5:12Google Scholar
  22. 22.
    Mehta AC (1994) Anal Proc 31:245Google Scholar
  23. 23.
    Giron D (1995) Thermochim Acta 248:1CrossRefGoogle Scholar
  24. 24.
    Laird T (1990) In: Kennewell PD (ed) Comprehensive medicinal chemistry, vol 1. Pergamon, Oxford, p 321Google Scholar
  25. 25.
    Curry SH, Thakker KM (1990) In: Taylor JB (ed) Comprehensive medicinal chemistry, vol 5. Pergamon, Oxford, p 545Google Scholar
  26. 26.
    Yasui M (1995) Nippon Kessho Gakkaishi 37:69Google Scholar
  27. 27.
    Brittain HG (1997) J Pharm Sci 86:405CrossRefGoogle Scholar
  28. 28.
    Sato K (1989) Zesz Nauk-Politech Lodz, Fiz 9:5Google Scholar
  29. 29.
    Kitamura M (1991) Kagaku Kogaku 55:263Google Scholar
  30. 30.
    Kitamura M (1992) Funtai Kogaku Kaishi 29:118Google Scholar
  31. 31.
    Kocevar J (1993) Farm Vestn (Ljubljana) 44:55Google Scholar
  32. 32.
    Kitamura M (1994) Bunri Gijutsu 24:365Google Scholar
  33. 33.
    Boistelle R, Klein JP, Guyot-Hermann AM (1996) STP Pharma Prat 6:111Google Scholar
  34. 34.
    Yamamoto H, Harano Y (1995) Bunri Gijutsu 25:381Google Scholar
  35. 35.
    Lahav M, Leiserowitz L (1993) J Phys D: Appl Phys 26:B22CrossRefGoogle Scholar
  36. 36.
    Weissbuch I, Popovitz-Biro R, Lahav M, Leiserowitz L (1995) Acta Crystallogr B51:115Google Scholar
  37. 37.
    Haleblian JK (1975) J Pharm Sci 64:1269CrossRefGoogle Scholar
  38. 38.
    Byrn SR (1982) Solid-state chemistry of drugs. Academic Press, New YorkGoogle Scholar
  39. 39.
    Hoelgaard A, Møller N (1983) Int J Pharm 15:213CrossRefGoogle Scholar
  40. 40.
    Caira MR, Nassimbeni LR, Van Oudtshoorn B (1993) J Pharm Sci 82:1006CrossRefGoogle Scholar
  41. 41.
    Burger A (1995) NATO Advanced research workshop crystals:Supramolecular materials. Sestri Levante, ItalyGoogle Scholar
  42. 42.
    McCrone WC (1965) Polymorphism. In: Fox D, Labes MM, Weissberger (eds) Physics and chemistry of the organic solid state. Interscience, New York p 726Google Scholar
  43. 43.
    Khoshkhoo S, Anwar J (1993) J Phys D: Appl Phys 26:B90CrossRefGoogle Scholar
  44. 44.
    Bartell LS (1995) J Phys Chem 99:1080CrossRefGoogle Scholar
  45. 45.
    Merlo M, Santos A, Gago Duport L (1993) Mater Res Soc Sympos Proc 290:317Google Scholar
  46. 46.
    Chakraborty D, Bhatia SK (1996) Ind Eng Chem Res 35:1985CrossRefGoogle Scholar
  47. 47.
    Morin B, Elder KR, Sutton M, Grant M (1995) Phys Rev Lett 75:2156CrossRefGoogle Scholar
  48. 48.
    Alfonso GC, Moretti P, Pallenzona P, Yin J (1995) Opt Eng (Bellingham, Wash) 34:3385CrossRefGoogle Scholar
  49. 49.
    Tiller WA (1986) J Cryst Growth 76:607CrossRefGoogle Scholar
  50. 50.
    Caira MR, Nassimbeni LR (1996) In: MacNicol DD, Toda F, Bishop R (eds) Comprehensive supramolecular chemistry, vol 6. Pergamon Press, Oxford, chap 25Google Scholar
  51. 51.
    Cardew PT, Davey RJ (1985) Proc R Soc London A398:415Google Scholar
  52. 52.
    Berkovitch-Yellin Z (1985) J Am Chem Soc 107:8239CrossRefGoogle Scholar
  53. 53.
    Kitamura M (1993) J Chem Eng Jpn 26:303CrossRefGoogle Scholar
  54. 54.
    Kitamura M, Furukawa H, Asaeda M (1994) J Cryst Growth 141:193CrossRefGoogle Scholar
  55. 55.
    Koga K, Kawakami R, Kagara K (1996) Kagaku Kogaku Ronbunshu 22:1174Google Scholar
  56. 56.
    Sudo S, Sato K, Harano Y (1991) J Chem Eng Japan 24:628CrossRefGoogle Scholar
  57. 57.
    Janik M, Malarski Z, Mrozinski J, Wajcht J, Zborucki Z (1991) J Crystallogr Spectr Res 21:519CrossRefGoogle Scholar
  58. 58.
    Bernstein J (1987) In: Desiraju GR (ed) Organic solid state chemistry. Elsevier, Amsterdam, p 471Google Scholar
  59. 59.
    Gerber JJ, Caira MR, Lötter AP (1993) J Crystallogr Spectr Res 23:863CrossRefGoogle Scholar
  60. 60.
    Pienaar EW, Caira MR, Lötter AP (1993) J Crystallogr Spectr Res 23:785CrossRefGoogle Scholar
  61. 61.
    Caira MR, Pienaar EW, Lötter AP (1996) Mol Cryst Liq Cryst 279:241CrossRefGoogle Scholar
  62. 62.
    Caira MR, Botha SA, Flanagan DR (1994) J Chem Crystallogr 24:95CrossRefGoogle Scholar
  63. 63.
    Allen FH, Trotter J (1971) J Chem Soc B 1073Google Scholar
  64. 64.
    Bernstein J, Etter MC, MacDonald JC (1990) J Chem Soc Perkin Trans 2 695Google Scholar
  65. 65.
    Gavezzotti A, Filippini G (1997) In: Gavezzotti A (ed) Theoretical aspects and computer modeling of the molecular solid state, vol 1. Wiley, New York, chap 3Google Scholar
  66. 66.
    Gavezzotti A (1991) J Am Chem Soc 113:4622CrossRefGoogle Scholar
  67. 67.
    Gdanitz RJ (1992) Chem Phys Lett 190:391CrossRefGoogle Scholar
  68. 68.
    Karfunkel HR, Gdanitz RJ, Leusen FJJ (1994) Comput Aided Mat Des 1:185Google Scholar
  69. 69.
    Perlstein J (1994) J Am Chem Soc 116:11,420Google Scholar
  70. 70.
    Leusen FJJ (1996) J Cryst Growth 166:900CrossRefGoogle Scholar
  71. 71.
    Baur WH, Kassner D (1992) Acta Crystallogr B48:356Google Scholar
  72. 72.
    Gavezzotti A, Filippini G (1996) J Am Chem Soc 118:7153CrossRefGoogle Scholar
  73. 73.
    Thiery M-M, Rerat C (1996) J Chem Phys 104:9079CrossRefGoogle Scholar
  74. 74.
    Toscani S, Dzyabchenko A, Agafonov V, Dugue J, Ceolin R (1996) Pharm Res 13:151CrossRefGoogle Scholar
  75. 75.
    Lukasheva NV, Sariban A, Mozel T, Brikman Y (1996) Vysokomol Soedin. Ser A Ser B 38:688Google Scholar
  76. 76.
    Williams DE (1996) Acta Crystallogr A52:326Google Scholar
  77. 77.
    Peeters A, Van Alsenoy C, Lenstra ATH, Geise HJ ( 1995) J Chem Phys 103:6608CrossRefGoogle Scholar
  78. 78.
    Gavezzotti A (1994) Acc Chem Res 27:309CrossRefGoogle Scholar
  79. 79.
    Gavezzotti A, Filippini G (1995) J Am Chem Soc 117:12,299CrossRefGoogle Scholar
  80. 80.
    Kuhnert-Brandstätter M (1971) Thermomicroscopy in the analysis of pharmaceuticals. Pergamon, New YorkGoogle Scholar
  81. 81.
    Haleblian J, McCrone WC (1969) J Pharm Sci 58:911CrossRefGoogle Scholar
  82. 82.
    Borka L (1974) Acta Pharm Suecica 11:295Google Scholar
  83. 83.
    Caira MR, Gifford Nash K, Nassimbeni LR (1995) Ann Congr Acad Pharm Sci 16th. Bloemfontein, South Africa. Abstract P28Google Scholar
  84. 84.
    Lerk CF, Andreae AC, De Boer AH, Bolhuis GK, Zuurman K, De Hoog P, Kussendrager K, Van Leverink J (1983) J Pharm Pharmacol 35:747Google Scholar
  85. 85.
    Fachaux JM, Guyot-Hermann A-M, Guyot JC, Conflant P, Drache M, Huvenne JP, Bouche R (1992) Congr Int Technol Pharm 6th 5:213Google Scholar
  86. 86.
    Shakhtshneider TP, Boldyrev VV (1993) Drug Dev Ind Pharm 19:2055CrossRefGoogle Scholar
  87. 87.
    Pirttimaki J, Laine E, Ketolainen J, Paronen P (1993) Int J Pharm 95:93CrossRefGoogle Scholar
  88. 88.
    Otsuka M, Matsuda Y (1990) Pharm Tech Jpn 6:977Google Scholar
  89. 89.
    Otsuka M, Matsuda Y (1993) Drug Dev Ind Pharm 19:2241CrossRefGoogle Scholar
  90. 90.
    Otsuka M, Otsuka K, Kaneniwa N (1994) Drug Dev Ind Pharm 20:1649CrossRefGoogle Scholar
  91. 91.
    Gubskaya AV, Chishko KA, Lisnyak YV, Blagoy YP (1995) Drug Dev Ind Pharm 21:1965CrossRefGoogle Scholar
  92. 92.
    Mullins JD, Macek TJ (1967) J Pharm Sci 56:847CrossRefGoogle Scholar
  93. 93.
    Ogawa K, Yui T (1994) Biosci Biotechnol Biochem 58:968CrossRefGoogle Scholar
  94. 94.
    Paukszta D, Garbarczyk J, Sterzynski T (1991) Int Union Crystallogr, Crystallogr Symp 4:192Google Scholar
  95. 95.
    Sayapina OV, Koshkin VM (1990) Pis’ma Zh Tekh Fiz 16:58Google Scholar
  96. 96.
    Hamill GP, Yost EA, Sandman DJ (1992) Mol Cryst Liq Cryst Sci Technol Sect A 211:339CrossRefGoogle Scholar
  97. 97.
    Chan HK, Gonda I (1989) J Cryst Growth 94:488CrossRefGoogle Scholar
  98. 98.
    Caira MR (1994) J Chem Crystallogr 24:695CrossRefGoogle Scholar
  99. 99.
    Bettinetti GP, Giordano F, La Manna A, Giuseppetti G (1974) Il Farmaco-EdPr 29:493Google Scholar
  100. 100.
    West AR (1996) Basic solid state chemistry. Wiley, ChichesterGoogle Scholar
  101. 101.
    Himes VL, Mighell AD, De Camp WH (1981) Acta Crystallogr B37:2242Google Scholar
  102. 102.
    Lowes MM, Caira MR, Lötter AP, Van der Watt JG (1987) J Pharm Sci 76:744CrossRefGoogle Scholar
  103. 103.
    Van Tonder EC, Caira MR, Botha SA, Lötter AP (1990) Int J Pharm 63:35CrossRefGoogle Scholar
  104. 104.
    Flynn JH, Wall LA (1966) Polym Lett 4:323CrossRefGoogle Scholar
  105. 105.
    Bourne SA, Caira MR, Nassimbeni LR, Shabalala I (1994) J Pharm Sci 83:887CrossRefGoogle Scholar
  106. 106.
    Caira MR, Nassimbeni LR, Timme M (1995) J Pharm Sci 84:884CrossRefGoogle Scholar
  107. 107.
    Burger A (1982) Acta Pharm Technol 28:1Google Scholar
  108. 108.
    Richardson MF, Yang Q-C, Novotny-Bregger E, Dunitz JD (1990) Acta Crystallogr B46:653Google Scholar
  109. 109.
    Acharya KR, Kuchela KN, Kartha G (1982) J Crystallogr Spectr Res 12:369CrossRefGoogle Scholar
  110. 110.
    Caira MR, Mohamed R (1992) Acta Crystallogr B48:492Google Scholar
  111. 111.
    Chang L-C, Caira MR, Guillory JK (1995) J Pharm Sci 84:1169CrossRefGoogle Scholar
  112. 112.
    Caira MR, Guillory JK, Chang L-C (1995) J Chem Crystallogr 25:393CrossRefGoogle Scholar
  113. 113.
    Suleiman MS, Najib NM (1989) Int J Pharm 50:103CrossRefGoogle Scholar
  114. 114.
    Yuan XB, Jiang DH, Shen HB, Ding HL (1991) Yaoxue Xuebao 26:152Google Scholar
  115. 115.
    Bishop R, Dance IG (1991) In: Atwood JL, Davies JED, MacNicol DD (eds) Inclusion compounds, vol 4. Oxford University Press, Oxford, p 1Google Scholar
  116. 116.
    Ung AT, Bishop R, Craig DC, Dance IG, Scudder ML (1993) Tetrahedron 49:639CrossRefGoogle Scholar
  117. 117.
    Babkov LM, Puchkovskaya GA (1993) Khim Fiz 12:944Google Scholar
  118. 118.
    Ciurczak EW (1987) Appl Spectrosc Rev 23:147CrossRefGoogle Scholar
  119. 119.
    Aldridge PK, Evans CL, Ward HW II, Colgan ST, Boyer N, Gemperline PJ (1996) Anal Chem 68:997CrossRefGoogle Scholar
  120. 120.
    Colombo L, Volovsek V, Furic K, Durig JR (1990) J Raman Spectrosc 21:169CrossRefGoogle Scholar
  121. 121.
    Ohno K, Yoshida H, Matsuura H (1996) Spectrochim Acta 52 A:1377Google Scholar
  122. 122.
    Glusker JP, Trueblood KN (1985) Crystal structure analysis, a primer, 2nd edn. Oxford University Press, New YorkGoogle Scholar
  123. 123.
    Ladd MFC, Palmer RA (1985) Structure determination by X-ray crystallography, Plenum New YorkGoogle Scholar
  124. 124.
    Hope H (1994) X-ray crystallography:a fast, first-resort analytical tool. In: Karlin KD (ed) Progr Inorg Chem. Wiley, New York, p 1CrossRefGoogle Scholar
  125. 125.
    The United States Pharmacopeia 23 (1995) The United States Pharmacopeial Convention Inc, Rockville MD p 1843Google Scholar
  126. 126.
    Kidd WC, Varlashkin P, Li C-Y (1993) Powder Diffr 8:180Google Scholar
  127. 127.
    Bar I, Bernstein J (1985) J Pharm Sci 74:255CrossRefGoogle Scholar
  128. 128.
    Sciesinska E, Mayer J, Natkaniec I, Sciesinski J (1989) Acta Phys Pol A76:617Google Scholar
  129. 129.
    Mazeau K, Winter WT, Chanzy H (1994) Macromolecules 27:7606CrossRefGoogle Scholar
  130. 130.
    Wojcik G, Jakubowski B, Szostak MM, Holderna-Matuszkiewicz K, Mayer J, Natkaniec I (1991) Kryszt Mol’91 Mater Ogolnopol Konf, p 169Google Scholar
  131. 131.
    Wojcik G, Jakubowski B, Szostak MM, Holderna-Natkaniec K, Mayer J, Natkaniec I (1992) Phys Status Solidi A134:139Google Scholar
  132. 132.
    Martinez-Oharriz MC, Martin C, Goni MM, Rodriguez-Espinosa C, Tros de Ilarduya-Apaolaza MC, Sanchez M (1994) J Pharm Sci 83:174CrossRefGoogle Scholar
  133. 133.
    Kristl A, Srcic S, Vrecer F, Sustar B, Vojnovic D (1996) Int J Pharm 139:231CrossRefGoogle Scholar
  134. 134.
    Lefebvre C, Guillaume F, Bouche R, Bouaziz R, Guyot JC (1989) 5th Congr Int Technol Pharm 1:211Google Scholar
  135. 135.
    Madan T, Kakkar AP (1994) Drug Dev Ind Pharm 20:1571CrossRefGoogle Scholar
  136. 136.
    Mitra AK, Ghosh LK, Gupta BK (1993) Drug Dev Ind Pharm 19:971CrossRefGoogle Scholar
  137. 137.
    Wojcik G, Giermanska-Kahn J, Marqueton Y, Foulon M (1995) Acta Phys Pol A88:339Google Scholar
  138. 138.
    Mayer J, Rachwalska M, Sciesinska E, Sciesinski J (1990) J Phys (Paris) 51:857CrossRefGoogle Scholar
  139. 139.
    Burger A, Koller KT (1996) Sci Pharm 64:293Google Scholar
  140. 140.
    Toscani S, Thoren S, Agafonov V, Ceolin R, Dugue J (1995) Pharm Res 12:1453CrossRefGoogle Scholar
  141. 141.
    Lourdin D, Roux AH, Grolier JPE (1991) Calorim Anal Therm 22:151Google Scholar
  142. 142.
    Hongisto V, Lehto V-P, Laine E (1996) Thermochim Acta 276:229CrossRefGoogle Scholar
  143. 143.
    Rietveld HM (1969) J Appl Crystallogr 2:65CrossRefGoogle Scholar
  144. 144.
    Estermann MA, McCusker LB, Baerlocher C (1992) J Appl Crystallogr 25:539CrossRefGoogle Scholar
  145. 145.
    Harris KDM, Tremayne M, Lightfoot P, Bruce PG (1994) J Am Chem Soc 116:3543CrossRefGoogle Scholar
  146. 146.
    Karfunkel HR, Wu ZJ, Burkhard A, Rihs G, Sinnreich D, Buerger HM, Stanek J (1996) Acta Crystallogr B52:555Google Scholar
  147. 147.
    Louër D, Louër M, Dzyabchenko VA, Agafonov V, Ceolin R (1995) Acta Crystallogr B51:182Google Scholar
  148. 148.
    Helliwell JR, Helliwell M (1996) J Chem Soc, Chem Commun 1595Google Scholar
  149. 149.
    MacCalman ML, Roberts KJ (1995) J Appl Crystallogr 28:620CrossRefGoogle Scholar
  150. 150.
    Yamanobe T, Komoto T, Sakaino Y (1996) Mol Cryst Liq Cryst 276:273CrossRefGoogle Scholar
  151. 151.
    Arishima T, Sugimoto K, Kiwata R, Mori H, Sato K (1996) J Am Oil Chem Soc 73:1231CrossRefGoogle Scholar
  152. 152.
    Rao RC (1992) Spectra 2000 166:33Google Scholar
  153. 153.
    Riddell FG, Bruce PG, Lightfoot P, Rogerson M (1994) J Chem Soc, Chem Commun 209Google Scholar
  154. 154.
    Ojala WH, Etter MC (1992) J Am Chem Soc 114:10,288CrossRefGoogle Scholar
  155. 155.
    Friedlander P (1879) Z Kristallogr 3:169Google Scholar
  156. 156.
    Gallagher HG, Sherwood JN (1996) J Chem Soc Faraday Trans 92:2107CrossRefGoogle Scholar
  157. 157.
    Davey RJ, Maginn SJ, Andrews SJ, Black SN, Buckley AM, Cottier D, Dempsey P, Plowman R, Rout JE, Stanley DR, Taylor A (1994) J Chem Soc Faraday Trans 90:1003CrossRefGoogle Scholar
  158. 158.
    Seebach D (1990) Angew Chem Int Ed Engl 29:1320CrossRefGoogle Scholar
  159. 159.
    Ngooi T-K, McGolrick JD, Antczak C, Tindall JLA (1994) CA 121:263,695eGoogle Scholar
  160. 160.
    Maryanoff CA (1995) CA 122:240,076 kGoogle Scholar
  161. 161.
    Shum SP, Pastor SD (1996) CA 124:246,949 kGoogle Scholar
  162. 162.
    Ibragimov BT, Talipov SA (1994) J Incl Phenom Mol Recognit Chem 17:325CrossRefGoogle Scholar
  163. 163.
    Ibragimov BT, Beketov K, Makhkamov K, Weber E (1997) J Chem Soc Perkin Trans 2:1349Google Scholar
  164. 164.
    Nakano Sada Miyata M (1996) J Chem Soc, Chem Commun 989Google Scholar
  165. 165.
    Weissbuch I, Zbaida D, Addadi L, Leiserowitz L, Lahav M (1987) J Am Chem Soc 109:1869CrossRefGoogle Scholar
  166. 166.
    Huang K-S, Britton D, Etter MC, Byrn SR (1995) J Mater Chem 5:379CrossRefGoogle Scholar
  167. 167.
    Weinbach SP, Weissbuch I, Kjaer K, Bouwman WG, Nielsen JA, Lahav M, Leiserowitz L (1995) Adv Mater 7:857CrossRefGoogle Scholar
  168. 168.
    Carter PW, Ward MD (1993) J Am Chem Soc 115:11,521Google Scholar
  169. 169.
    Bonafede SJ, Ward MD (1995) J Am Chem Soc 117:7853CrossRefGoogle Scholar

Copyright information

© Springer Verlag Berlin Heidelberg 1998

Authors and Affiliations

  • Caira Mino R. 
    • 1
  1. 1.Department of ChemistryUniversity of Cape TownRondeboschSouth Africa

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