HULA-TWIST IN PHOTOISOMERIZATION: ORGANIC SYSTEMS

doi:10.7517/j.issn.1674-0475.2002.02.81

Abstract

Abstract: Literature examples of photoisomerization involving organic compounds under confined conditions are summarized.They are shown to be consistent with the Hula twist mechanism of isomerization.Thus,the results support the theory that such a volume conserving reaction mechanism is favored for photoreactions of substrates under conditions where the medium plays a significant role,i.e.,a supramoleclar process.

Key words: photoisomerization, Hula twist, confined media, diarylethylenes, polyenes

CLC Number:

O644

Robert S.H.LIU. HULA-TWIST IN PHOTOISOMERIZATION: ORGANIC SYSTEMS[J]. Imaging Science and Photochemistry, 2002, 20(2): 81-87.

References

[1] Liu R S H,Asato A E.The primary process of vision and the structure of bathorhodopsin:a mechanism for photoisomerzation of polyenes[J].Proc.Natl.Acad.Sci.USA,1985,82:259-263.
[2] Liu R S H,Browne D T.A bioorganic view of the chemistry of vision:H.T.-n and B.P.-m,n mechanisms for reactions of confined,anchored polyenes[J].Acc.Chem.Res.,1986,19:42-48.
[3] Liu R S H,Hammond G S.The case of medium-dependent dual mechanisms for photoisomerization:one-bond-flip and hula-twist[J].Proc.Natl.Acad.Sci.USA,2000,97:11153-11158.
[4] Liu R S H.Photoisomerization by hula-twist:a fundamental supramolecular photochemical reaction[J].Acc.Chem.Res.,2001,34:555-562.
[5] Liu R S H,Hammond G S.Examples of hula-twist in photochemical cis,trans isomerization[J].Chem.Euro.J.,2001,7:4536-4545.
[6] Liu R S H.Hula-twist in photoisomerization:photoactive biopigment[M].Pure Appl.Chem.,submitted.
[7] Squillacote M E,Sheridan R S,Chapman O L,Anet F A L.Planar s-cis-1,e-butadiene[J].J.Am.Chem.Soc.,1975,101:3657-3659.
[8] Akerman J R,Forman S A,Hossain M,Kohler B.S-cis octatetraene: photoproduction and spectroscopic properties[J].J.Chem.Phys.,1984,80:39-44.
[9] Squillacote M E,Semple T C.Photochemistry of s-cis acyclic 1,3-dienes[J].J.Am.Chem.Soc.,1990,112:5546-5551.
[10] Mazzucato U,Momicchioli F.Rotational isomerization in trans-1,2-diarylethylenes[J].Chem.Rev.,1991,91:1679-1719.
[11] Alfimov M V,Razumov V F,Rachinsky A G,Listvan V N,Scheck Yu B.Photochemical production of non-equilibrium conformers in glassy solutions of diarylethylenes at 77K[J].Chem.Phys.Lett.,1983,101:593-597.
[12] Castel N,Fischer E.Frozen-in non-equilibrium rotamers in 1,2-diarylethylenes obtained by low-temperature irradiation[J].J.Mol.Struct.,1985,127:159-166.
[13] Muller A M,Lochbrunner S,Schmid W E,Fuss W.Low-temperature photochemistry of previtamin D:hula-twist isomerization of a triene[J].Angew.Chem.Int.Ed.,1998,37:505-507.
[14] Kaupp G,Schmeyers J.The solid state E/Z-photoisomerization of 1,2-dibenzoylethene[J].J.Photochem.Photobiol.Sec B,2000,59:15-19.
[15] Mizutani T,Ikegami M,Nagahata R,Arai T.The first synthesis of stilbene dendrimers and their photochemical trans,cis isomerization[J].Chem.Lett.,2001,1014-1015.
[16] Ingjald A,Sandros K,Sundahl M,Wennerstrom O.Cis-trans photoisomerization of bis-stilbenes with ethylene bridges[J].J.Phys.Chem.,1993,97:1920-1923.
[17] Van der Meer M J,Zhang H,Rettig W,Glasbeck M.Femto-and picosecond fluorescence studies of solvation and nonradiative deactivation of ionic styryl dyes in liquid solution[J].Chem.phys.Lett.,2000,320:673-680.
[18] Waldeck D H.Photoisomerization dynamics of stilbenes[J].Chem.Rev.,1990,91:415-436.
[19] Doany F E,Hochstrasser R M,Greene B I.Isomerization inter mediates in solution phase photochemistry of stilbenes[M].SPIE, 1985,533:25-29.
[20] Drickmar H G.Pressure tuning spectroscopy[J].Acc.Chem.Res.,1986,19:329-334.