Direct Synthesis of Poly(arylmethyl Sulfone) Monodendrons

Abstract

Synthetic efforts toward poly(arylmethyl sulfone) dendrimers are described. A molecule designed to function as a protected AB₂ monomer, phenyl 3,5-bis(chloromethyl)benzenesulfonate was synthesized in four steps from dimethyl 5-sulfoisophthalate in 59% overall yield. This monomer was coupled to sodium benzenesulfinate to give the generation 1 monodendron, phenyl 3,5-bis­-(phenylsulfonylmethyl)benzenesulfonate. However, deprotection of the generation 1 monodendron by literature methods of reduction and hydrolysis were not successful.

Key words

sulfones - polymers - dendrimers

References

• 1a For a series of reviews of dendrimers recently published, see: Prog. Polym. Sci.  2005,  30:  217 
• 1b Jikei M. Kakimoto M.-A. Prog. Polym. Sci.  2001,  26:  1233 
• 1c Tomalia DA. Frechet JMJ. J. Polym. Sci., Part A: Polym. Chem.  2002,  40:  2719 
• 1d Sheiko SS. Moller M. Top. Curr. Chem.  2001,  212:  137 
• 1e Inoue K. Prog. Polym. Sci.  2000,  25:  453 
• 1f Hult A. Johansson M. Malmstrom E. Adv. Polym. Sci.  1999,  143:  1 
• 1g Bosman AW. Janssen HM. Meijer EW. Chem. Rev.  1999,  99:  1665 
• 2a Encyclopedia of Polymer Science and Engineering   John Wiley; New York: 1988. 
• 2b Polymeric Materials Encyclopedia   CRC Press; Boca Raton: 1996. 
• 2c Polymer Handbook   3rd ed.:  Brandrup J. Immergut EH. Wiley-Interscience; New York: 1989. 
• 3a Jikei M. Hu Z. Kakimoto M. Imai Y. Macromolecules  1996,  29:  1062 
• 3b Miller TM. Neenan TX. Kwock EW. Stein SM. J. Am. Chem. Soc.  1993,  115:  356 
• 3c Mellace A. Hanson JE. Griepenburg J. Chem. Mater.  2005,  17:  1812 
• 3d Chang Y. Kwon Y. Park K. Kim C. Korea Polym. J.  2000,  8:  142 
• 4 Chow HF. Ng MK. Leung CW. Wang GX. J. Am. Chem. Soc.  2004,  126:  12907 
• 5 Hawker CJ. Frechet JMJ. J. Am. Chem. Soc.  1990,  112:  7638 
• 6a Novembre AE. Hanson JE. Kometani JM. Tai WW. Reichmanis E. Thompson LF. West RJ. Polym. Eng. Sci.  1992,  32:  1476 
• 6b Hanson JE. Jensen KH. Gargiulo N. Motta D. Pingor DA. Novembre AE. Mixon DA. Kometani JM. Knurek C. Microelectronics Technology: Polymers for Advanced Imaging and Packaging   Reichmanis E. Ober CK. MacDonald SA. Iwayanagi T. Nishikubo T. ACS Symposium Series 614; American Chemical Society; Washington DC: 1995.  p.137-148  
• 6c Organic Functional Group Preparations   2nd ed.:  Sandler SR. Karo W. Academic Press; New York: 1983.  Part I.
• 7 Tyler TL. Hanson JE. Chem. Mater.  1999,  11:  3452 
• 8 Hanson JE. Reichmanis E. Houlihan FM. Neenan TX. Chem. Mater.  1992,  4:  837 
• 9a Freudenberg K. Hess H. Justus Liebigs Ann. Chem.  1926,  448:  121 
• 9b Carter P. Stevens TS. J. Chem. Soc.  1961,  1743 
• 9c Lemal DM. Rave TW. McGregor SD. J. Am. Chem. Soc.  1963,  85:  1944 
• 9d Lemal DM. Rave TW. J. Am. Chem. Soc.  1965,  87:  393 
• 10a Sylwester AP. Dervan PB. J. Am. Chem. Soc.  1984,  106:  4648 
• 10b Michaelis A. Luzembourg K. Ber. Dtsch. Chem. Ges.  1893,  26:  2174 
• 10c Lwowski W. Reactive Intermediates   Jones M. Moss RA. Wiley; New York: 1985.  p.325-327  
• 10d Lemal DM. Nitrenes   Lwowski W. Wiley-Interscience; New York: 1970.  p.345-404