2003-06-01, English, Article, Journal or magazine article edition: Stereoselective [O.sub.2]-induced photoisomerization of all-trans-1,6-diphenyl-1,3,5-hexatriene.(Author Abstract) Saltiel, Jack; Krishnamoorthy, Govindarajan; Huang, Zhennian; ...

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Physical Description
  • Author Abstract
  • Magazine/​Journal article
Published
  • NRC Research Press, 2003 June
Language
  • English

Edition details

Title
  • Stereoselective [O.sub.2]-induced photoisomerization of all-trans-1,6-diphenyl-1,3,5-hexatriene.(Author Abstract)
Also Titled
  • Stereoselective [O.sub.2]-induced photoisomerization of all-trans-1,6-diphenyl-1,3,5-hexatriene.
Appears In
  • Canadian Journal of Chemistry, v.81, no.6, 2003 June, p.673(7) (ISSN: 0008-4042)
Author
  • Saltiel, Jack
  • Krishnamoorthy, Govindarajan
  • Huang, Zhennian
  • Ko, Dong-Hoon
  • Wang, Shujun
Published
  • NRC Research Press, 2003 June
Physical Description
  • Author Abstract
  • Magazine/​Journal article
Subjects
Target Audience
  • Academic
Summary
  • Irradiation of all-trans-1,6-diphenyl-1,3,5-hexatriene (ttt-DPH) in degassed acetonitrile (AN) gives ctt- and tct-DPH, relatively inefficiently, mainly via isomerization in the singlet excited state. The triplet contribution to the photoisomerization is small due to a very low intersystem crossing yield ([phi].sub.is] =​ 0.01). Central bond isomerization is quenched in the presence of air by a factor of 1.4, consistent with the expected quenching of the lowest singlet and triplet excited states by oxygen. However, the presence of air enhances terminal bond photoisomerization by nearly twofold. Triplet-sensitized ttt-DPH photoisomerization favors tct-DPH formation and is quenched by oxygen. It follows that the interaction of singlet-excited ttt-DPH with [O.sub.2] suppresses isomerization to tct-DPH but opens a new isomerization pathway to ctt-DPH. The presence of dimethylfuran, a singlet [O.sub.2] trap, has no effect on the photoisomerization, eliminating the possible involvement of singlet [O.sub.2] in this new reaction, ttt-DPH radical cations are ruled out as intermediates because the presence of fumaronitrile, which leads to their formation, suppresses both central and terminal bond photoisomerizations. In contrast to acetonitrile, ctt-DPH formation is quenched by oxygen in methylcyclohexane, suggesting the requirement of a polar environment. Strikingly different deuterium isotope effects distinguish the direct and [O.sub.2]-induced photoisomerization pathways. A comparative study of ttt-DPH-do with ttt-DPH-d2 and ttt-DPH-d4, involving deuteration of one and both terminal double bonds, reveals an inverse kinetic isotope effect ([k.sub.H.sup.ox]/​[k.sub.D.sup.ox]=​ 0.92) for the [O.sub.2]-induced reaction. An attractive mechanism for the new oxygen-induced photoisomerization involves charge transfer from the [S.sub.1] state of ttt-DPH to oxygen followed by collapse of the exciplex to either a zwitterionic or a biradicaloid species through bonding at one of the benzylic positions. Rotation about the new single bond in this intermediate followed by reversion to DPH and [O.sub.2] gives the observed result. Key words: diphenylhexatrienes, trans-cis photoisomerization, oxygen sensitization.
Terms of Use
  • COPYRIGHT 2003 NRC Research Press
Language
  • English
Database
  • Gale Academic OneFile
  • Gale General OneFile
  • Gale Expanded Academic
Identifier
  • 109178888

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CAVAL. CARM Centre. May not be open to the public brn.181082; Held; Vol. 52, no. 1 - v. 77; Jan. 1974 - 1999; Inc. Periodical; Journal, magazine, other English; French
Charles Sturt University. CSU Library - Electronic Resources (shared). Open to the public 000098168; Full Text Available; ProQuest Natural Science Journals New Platform - Available from 1998 until 2007 Periodical; Journal, magazine, other English; French
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Defence Science and Technology Group. DST Group Research Information Services - Melbourne. Not open to the public Serials; Vol. 29-v.68; 1951-1990; incomplete Periodical; Journal, magazine, other English; French
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James Cook University. Townsville Campus Library. Open to the public 104; <104>; Vol. 29 - v. 74; 1951 - 1996; Incomplete Periodical; Journal, magazine, other English; French
Macquarie University. Macquarie University Library. Open to the public 992055610802171; QD1 .C285; Vol. 29 (1951)-vol. 33 (1955); vol. 39 (1961)-vol. 83, no. 8 (2005); vol. 83, no. 10 (2005)-vol. 83, no. 12 (2005) Periodical; Journal, magazine, other English; French
Monash University. Monash University Library. Open to the public 99867301751; 540.5 C212; v. 29 (1951) to v.84 (2006) ; Incomplete ; Includes Indexes; Lacks: v. 52 (1974) ; v. 53, no. 1-6 (1975) ; v. 53, no. 13-24 (1975) ; v.54 (1976) to v. 55 (1977) ; v. 73 (1995) to v. 77 (1999); HA; XST-TE Periodical; Journal, magazine, other English; French
National Library of Australia. Open to the public 2333488; S 540.5 CAN; Vol. 29-v. 64 (1951-1986) Periodical; Journal, magazine, other English; French
NSW Department of Industry. DTIRIS: Electronic Resources Library. Not open to the public V 29 1951 - V 75 1997 Periodical; Journal, magazine, other English; French
RMIT University. RMIT University Library. Open to the public 9912892330001341; PER 540 C212; Incomplete. Held in Storage. Request from <a href=http://www.rmit.edu.au/library/dds target=_blank>Document Delivery</a>; v. 51, no. 1 (Jan. 1, 1973)-v. 70, no. 12 (Dec. 1992) Periodical; Journal, magazine, other English; French
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University of Newcastle. University of Newcastle Library. Open to the public 540.5/9; Vol. 29, no. 1-v. 75, no. 12; Jan. 1951-Dec. 1997 Periodical; Journal, magazine, other English; French
University of New England. Dixson Library. Open to the public 1024-67060; <1024-67060>; P540.5/CAN <1024-67060>; V.29 (1951)- Periodical; Journal, magazine, other English; French
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National Library of Australia. Open to the public 2333488; S 540.5 CAN; Vol. 29-v. 64 (1951-1986) Periodical; Journal, magazine, other English; French
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Charles Sturt University. CSU Library - Electronic Resources (shared). Open to the public 000098168; Full Text Available; ProQuest Natural Science Journals New Platform - Available from 1998 until 2007 Periodical; Journal, magazine, other English; French
Cumberland Council. Auburn Library. Open to the public Periodical; Journal, magazine, other English; French
Macquarie University. Macquarie University Library. Open to the public 992055610802171; QD1 .C285; Vol. 29 (1951)-vol. 33 (1955); vol. 39 (1961)-vol. 83, no. 8 (2005); vol. 83, no. 10 (2005)-vol. 83, no. 12 (2005) Periodical; Journal, magazine, other English; French
NSW Department of Industry. DTIRIS: Electronic Resources Library. Not open to the public V 29 1951 - V 75 1997 Periodical; Journal, magazine, other English; French
Shellharbour City Council. Shellharbour City Library Service. Open to the public Periodical; Journal, magazine, other English; French
Shore School. Boer War Contingent Memorial Library. Not open to the public Periodical; Journal, magazine, other English; French
Southern Cross University. University Library Lismore. Open to the public Electronic resource - Check catalogue for holdings Periodical; Journal, magazine, other English; French
State Library of NSW. Open to the public Held; 1951-1991 Periodical; Journal, magazine, other English; French
St Vincent's Hospital (Sydney). Walter McGrath Library. Not open to the public (EbpS)ebs515368; held Periodical; Journal, magazine, other English; French
The University of Sydney. University of Sydney Library. Open to the public .b1156507x; held Periodical; Journal, magazine, other English; French
University of Newcastle. University of Newcastle Library. Open to the public 540.5/9; Vol. 29, no. 1-v. 75, no. 12; Jan. 1951-Dec. 1997 Periodical; Journal, magazine, other English; French
University of New England. Dixson Library. Open to the public 1024-67060; <1024-67060>; P540.5/CAN <1024-67060>; V.29 (1951)- Periodical; Journal, magazine, other English; French
University of Wollongong. University of Wollongong Library. Open to the public Online access. Not available for document delivery Periodical; Journal, magazine, other English; French
Western Sydney University. Campbelltown Campus Library. Open to the public 399266; 540.5 4 Periodical; Journal, magazine, other English; French
Western Sydney University. Penrith Campus Library. Open to the public 399266; Online version Periodical; Journal, magazine, other English; French
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Department of Agriculture and Fisheries Qld. Dept of Agriculture and Fisheries Qld Research Information Service. Not open to the public STACK; vol.29,no.1-v.31; 1951-1953 Periodical; Journal, magazine, other English; French
James Cook University. Townsville Campus Library. Open to the public 104; <104>; Vol. 29 - v. 74; 1951 - 1996; Incomplete Periodical; Journal, magazine, other English; French
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Flinders University. Flinders University Central Library. Open to the public 9957369701771; 540.5 C21 Periodical; Journal, magazine, other English; French
University of Adelaide. Barr Smith Library. Open to the public 9996397001811; MICROFICHE PER 86; v.60(1982)-v.69(1991) Periodical; Journal, magazine, other English; French
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Bialik College. Bialik College Library. Not open to the public Periodical; Journal, magazine, other English; French
CAVAL. CARM Centre. May not be open to the public brn.181082; Held; Vol. 52, no. 1 - v. 77; Jan. 1974 - 1999; Inc. Periodical; Journal, magazine, other English; French
Defence Science and Technology Group. DST Group Research Information Services - Melbourne. Not open to the public Serials; Vol. 29-v.68; 1951-1990; incomplete Periodical; Journal, magazine, other English; French
Monash University. Monash University Library. Open to the public 99867301751; 540.5 C212; v. 29 (1951) to v.84 (2006) ; Incomplete ; Includes Indexes; Lacks: v. 52 (1974) ; v. 53, no. 1-6 (1975) ; v. 53, no. 13-24 (1975) ; v.54 (1976) to v. 55 (1977) ; v. 73 (1995) to v. 77 (1999); HA; XST-TE Periodical; Journal, magazine, other English; French
RMIT University. RMIT University Library. Open to the public 9912892330001341; PER 540 C212; Incomplete. Held in Storage. Request from <a href=http://www.rmit.edu.au/library/dds target=_blank>Document Delivery</a>; v. 51, no. 1 (Jan. 1, 1973)-v. 70, no. 12 (Dec. 1992) Periodical; Journal, magazine, other English; French
The University of Melbourne. The University Library. Open to the public Ch P CANA; v.29-v.84; 1951-2006 Periodical; Journal, magazine, other English; French
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