Extending the short and long wavelength limits of bacteriochlorin near-infrared absorption via dioxo- and bisimide-functionalization

The Journal of Physical Chemistry. B
Pothiappan VairaprakashDewey Holten

Abstract

Six new bacteriochlorins expanding the range of the strong near-infrared (NIR) absorption (Qy band) to both shorter and longer wavelengths (∼690 to ∼900 nm) have been synthesized and characterized. The architectures include bacteriochlorin-bisimides that have six-membered imide rings spanning the 3,5- and 13,15-macrocycle positions or five-membered imide rings spanning the β-pyrrolic 2,3- and 12,13-positions. Both bisimide types absorb at significantly longer wavelength than the bacteriochlorin precursors (no fused rings), whereas oxo-groups at the 7- or 7,17-positions shift the Qy band to a new short wavelength limit. Surprisingly, bacteriochlorin-bisimides with five-membered β-pyrrolic-centered imide rings have a Qy band closer to that of six-membered bacteriochlorin-monoimides. However, the five-membered bisimides (versus the six-membered bacteriochlorin-monoimides) have significantly enhanced absorption intensity that is paralleled by an ∼2-fold higher fluorescence yield (∼0.16 vs ∼0.07) and longer singlet excited-state lifetime (∼4 ns vs ∼2 ns). The photophysical enhancements derive in part from mixing of the lowest unoccupied frontier molecular orbitals of the five-membered imide ring with those of the bacteriochlorin fra...Continue Reading

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Citations

Oct 28, 2015·Photochemistry and Photobiology·Eunkyung YangDewey Holten
Jan 15, 2016·The Journal of Physical Chemistry. a·Hyun Suk KangDavid F Bocian
Aug 1, 2015·The Journal of Physical Chemistry. B·Tuba SahinJonathan S Lindsey
Apr 15, 2016·The Journal of Organic Chemistry·Michael Anthony HylandChristian Brückner
Aug 31, 2016·Topics in Current Chemistry·Andrea BarbieriNicola Armaroli
Aug 9, 2016·Chemical Reviews·Masahiko Taniguchi, Jonathan S Lindsey
Dec 21, 2016·Journal of the American Chemical Society·Matthew J Guberman-PfefferChristian Brückner
Jan 8, 2017·Biomedicine & Pharmacotherapy = Biomédecine & Pharmacothérapie·Jianjun ChengYingxue Jin
Apr 20, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Muthyala Nagarjuna ReddyJonathan S Lindsey
Dec 18, 2015·Organic & Biomolecular Chemistry·Francisco F de AssisKleber T de Oliveira
May 10, 2017·Photochemistry and Photobiology·Christian Brückner
Jun 27, 2018·Physical Chemistry Chemical Physics : PCCP·Bowen YangChristian Brückner
Jan 31, 2017·New Journal of Chemistry = Nouveau Journal De Chimie·Nuonuo ZhangJonathan S Lindsey
Jun 22, 2021·Photochemistry and Photobiology·Kathy-Uyen NguyenJonathan S Lindsey
Oct 22, 2020·The Journal of Organic Chemistry·Nivedita ChaudhriChristian Brückner
Sep 17, 2016·The Journal of Physical Chemistry. a·Javad AmanpourDewey Holten
Oct 19, 2017·Journal of the American Chemical Society·Yusong BaiMichael J Therien
Feb 8, 2020·Inorganic Chemistry·David SchnableChristian Brückner
Jul 31, 2019·The Journal of Physical Chemistry. a·Matthew J Guberman-PfefferJosé A Gascón
Aug 29, 2018·The Journal of Physical Chemistry. a·Jonathan M YuenDewey Holten
Sep 3, 2021·The Journal of Physical Chemistry. a·Jie RongDewey Holten

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