Design, synthesis and spectral studies of novel bile acid-arene conjugates: Trans to cis isomerization of azobenzene core controlled by bile acid hydrophobicity
Koivukorpi, J; Kolehmainen, E
| HERO ID | 854583 |
|---|---|
| In Press | No |
| Year | 2008 |
| Title | Design, synthesis and spectral studies of novel bile acid-arene conjugates: Trans to cis isomerization of azobenzene core controlled by bile acid hydrophobicity |
| Authors | Koivukorpi, J; Kolehmainen, E |
| Journal | Journal of Molecular Structure |
| Volume | 875 |
| Issue | 1-3 |
| Page Numbers | 63-67 |
| Abstract | Four bile acid-arene conjugates, 1,4-bis[dimethyl(3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cliolan-24-amidoethyl)ammoniomethyl]benzene dibromide (1), 1,3,5-tris[dimetliyl(3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholan-24-amidoethyl)ammoniomethyl]benzene tribromide (2), bis{4-[dimethyl-(3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholan-24-amidoethyl)ammoniomethyl]phenyl}diazene dibromide (3), and bis{4-[dimethyl(3 alpha-hydroxy-5 beta-cholan-24-amidoethyl)ammoniomethyl]phenyl}diazene dibromide (4), have been synthesized in good yields, and their structures have been characterized by H-1, C-13, C-13 DEPT-135, PFG H-1, C-13 HMQC, PFG H-1, C-13 HMBC, and PFG H-1, N-15 HMBC NMR spectra. Their molecular weights and elemental compositions have been determined by ESI-TOF mass spectrometry and elemental analyses. Trans to cis isomerization of azobenzene derivatives 3 and 4 have also been studied. It was found that by increasing the hydrophobicity of bile acid moiety (from cholyl to lithocholyl) the trans to cis photoinduced isomerization tendency is increased in a protic solvent. (C) 2007 Elsevier B.V. All rights reserved. |
| Doi | 10.1016/j.molstruc.2007.03.058 |
| Wosid | WOS:000254765700010 |
| Url | http://linkinghub.elsevier.com/retrieve/pii/S0022286007003109 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Keyword | bile acid; p-xylene; mesitylene; azobenzene; trans to cis isomerization |
| Is Qa | No |