Synthesis and excited-state photodynamics of a chlorin-bacteriochlorin dyad--through-space versus through-bond energy transfer in tetrapyrrole arrays

Photochemistry and Photobiology
Chinnasamy MuthiahJonathan S Lindsey

Abstract

Understanding energy transfer among hydroporphyrins is of fundamental interest and essential for a wide variety of photochemical applications. Toward this goal, a synthetic free base ethynylphenylchlorin has been coupled with a synthetic free base bromobacteriochlorin to give a phenylethyne-linked chlorin-bacteriochlorin dyad (FbC-pe-FbB). The chlorin and bacteriochlorin are each stable toward adventitious oxidation because of the presence of a geminal dimethyl group in each reduced pyrrole ring. A combination of static and transient optical spectroscopic studies indicate that excitation into the Qy band of the chlorin constituent (675 nm) of FbC-pe-FbB in toluene results in rapid energy transfer to the bacteriochlorin constituent with a rate of approximately (5 ps)(-1) and efficiency of >99%. The excited bacteriochlorin resulting from the energy-transfer process in FbC-pe-FbB has essentially the same fluorescence characteristics as an isolated monomeric reference compound, namely a narrow (12 nm fwhm) fluorescence emission band at 760 nm and a long-lived (5.4 ns) Qy excited state that exhibits a significant fluorescence quantum yield (Phif=0.19). Förster calculations are consistent with energy transfer in FbC-pe-FbB occurring ...Continue Reading

References

May 18, 2000·The Journal of Organic Chemistry·J P StrachanJ S Lindsey
Oct 30, 2001·The Journal of Organic Chemistry·M TaniguchiJ S Lindsey
Oct 12, 2002·The Journal of Organic Chemistry·Masahiko TaniguchiJonathan S Lindsey
Jan 21, 2004·Journal of Photochemistry and Photobiology. B, Biology·Emma S Nyman, Paavo H Hynninen
Jul 23, 2004·Journal of Medicinal Chemistry·Michael R DettyStephen J Wagner
Dec 31, 2004·The Journal of Organic Chemistry·Masahiko TaniguchiJonathan S Lindsey
Jul 2, 2005·The Journal of Organic Chemistry·Han-Je Kim, Jonathan S Lindsey
Feb 14, 2006·The Journal of Physical Chemistry. B·Laurence PetitNino Russo
May 20, 2006·The Journal of Organic Chemistry·Joydev K LahaJonathan S Lindsey
May 20, 2006·The Journal of Organic Chemistry·Marcin PtaszekJonathan S Lindsey
Jul 21, 2006·The Journal of Physical Chemistry. B·Hooi Ling KeeDewey Holten
Aug 26, 2006·The Journal of Organic Chemistry·Joydev K LahaJonathan S Lindsey
Feb 3, 2007·The Journal of Physical Chemistry. B·Martin RegehlyBeate Röder
May 23, 2007·Chemistry : a European Journal·Thorsten KönekampFranz-Peter Montforts
Jun 15, 2007·The Journal of Organic Chemistry·Dazhong FanJonathan S Lindsey
Jun 26, 2007·The Journal of Organic Chemistry·Chinnasamy MuthiahJonathan S Lindsey
Sep 7, 2007·The Journal of Organic Chemistry·Chinnasamy MuthiahJonathan S Lindsey

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Citations

Jun 19, 2013·Chemical Reviews·Annette D Allen, Thomas T Tidwell
Dec 8, 2015·Journal of Porphyrins and Phthalocyanines·Doyoung RaJonathan S Lindsey
Aug 31, 2016·Topics in Current Chemistry·Andrea BarbieriNicola Armaroli
Jan 8, 2017·Biomedicine & Pharmacotherapy = Biomédecine & Pharmacothérapie·Jianjun ChengYingxue Jin
Aug 24, 2020·The Journal of Chemical Physics·Brian UtheMatthew Pelton
Feb 8, 2020·Physical Chemistry Chemical Physics : PCCP·Ying XiaMichael K H Leung
Jun 13, 2009·The Journal of Organic Chemistry·Olga MassJonathan S Lindsey
Jan 22, 2010·The Journal of Organic Chemistry·Michael KrayerJonathan S Lindsey
Sep 15, 2010·The Journal of Physical Chemistry. a·Soumyaditya MulaRaymond Ziessel
Mar 25, 2015·The Journal of Organic Chemistry·Adam MearesMarcin Ptaszek

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