Synthesis of 2-Benzyl-1,10-phenanthrolines Substituted by Sulfoxide or
Sulfone Groups as Potential Photochromic Compounds

Abstract

New 2-benzyl-1,10-phenanthrolines, substituted at the 2′ position by electron-withdrawing groups, were synthesized through nucleophilic substitution involving 2-chloro-1,10-phenanthroline and substituted benzyllithiums, respectively. The expected reversible photoinduced proton transfer reaction of such compounds were studied.

Key words

benzylation - heterocycles - metalations - sulfones - photochemistry

References

• 1a Shinohara S. Takeda J. Ooike T. Kurita S. J. Phys. Soc. Jpn.  1999,  68:  1725 
• 1b Houbrechts S. Clays K. Persoons A. Pikramenou Z. Lehn JM. Chem. Phys. Lett.  1996,  258:  485 
• 1c Corval A. Kuldova K. Eichen Y. Pikramenou Z. Lehn JM. Trommsdorff HP. J. Phys. Chem.  1996,  100:  19315 
• 1d Frank I. Grimme S. Peyerimhoff SD. J. Phys. Chem.  1996,  100:  16187 
• 1e Scherl M. Haarer D. Fischer J. Decian A. Lehn JM. Eichen Y. J. Phys. Chem.  1996,  100:  16175 
• 1f Eichen Y. Lehn JM. Scherl M. Haarer D. Caselegno R. Corval A. Kuldova K. Trommsdorff HP. J. Chem. Soc., Chem. Commun.  1995,  713 
• 2a Hardwick R. Mosher HS. Passailaigue P. J. Chem. Soc., Faraday Trans.  1960,  56:  44 
• 2b Klemm D. Klemm E. J. Prackt. Chem.  1978,  320:  551 
• 3 Heynderickx A. Samat A. Guglielmetti R. J. Heterocycl. Chem.  2001,  38:  737 
• 4 Taylor EC. Martin SF. J. Am. Chem. Soc.  1974,  96:  8095 
• 5 Corey EJ. Borror AL. Foglia T. J. Org. Chem.  1965,  30:  288 
• 6 Sigman DS. Wahl GM. Creighton DJ. Biochemistry  1972,  11:  2236 
• 7 Taylor DB. Callahan KP. Shaikh I. J. Med. Chem.  1975,  18:  1088 
• 8 Mathis JM. Pallenberg AJ. Synth. Commun  1997,  27:  2943 
• 9a Lüning U. Müller M. Chem. Ber.  1990,  123:  643 
• 9b Solladié N. Chambron JC. Sauvage JP. J. Am. Chem. Soc.  1999,  121:  3684 
• 10a Johnson MR. Bell D. Shanaman L. Heterocycles  1997,  45:  1059 
• 10b Fife TH. Pujari MP. J. Am. Chem. Soc.  1988,  110:  7790 
• 11 Labadie JW. Stille JK. J. Am. Chem. Soc.  1983,  105:  6129 
• 12 Desponds O. Schlosser M. J. Organomet. Chem.  1991,  409:  93 
• 13 Meyer JJ. Levoir P. Dubest R. Analyst (Cambridge U. K.)  1995,  120:  447