Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 20, Pages 13186-13193Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01860
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Funding
- National Science Foundation [OIA-1757220]
- Center for Chemical Innovation in Selective C-H Functionalization [CHE-1700982]
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A NIR II emissive dye was synthesized by the C-H bond functionalization of 1-methyl-2-phenylindolizine with 3,6-dibromoxanthene. The rhodindolizine (RhIndz) spirolactone product was nonfluorescent; however, upon opening of the lactone ring by the formation of the ethyl ester derivative, the fluorophore absorbs at 920 nm and emits at 1092 nm, which are both in the NIR II region. In addition, 4-cyanophenyl- (CNRhIndz) and 4-methoxyphenyl-substituted rhodindolizine (MeORhlndz) could also be prepared by the C-H activation reaction.
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