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. 2019 Oct 18;84(20):13186-13193.
doi: 10.1021/acs.joc.9b01860. Epub 2019 Sep 12.

Donor-Acceptor-Donor NIR II Emissive Rhodindolizine Dye Synthesized by C-H Bond Functionalization

Chathuranga S L Rathnamalala  1 , Jacqueline N Gayton  2 , Austin L Dorris  2 , Shane A Autry  2 , William Meador  2 , Nathan I Hammer  2 , Jared H Delcamp  2 , Colleen N Scott  1
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Donor-Acceptor-Donor NIR II Emissive Rhodindolizine Dye Synthesized by C-H Bond Functionalization

Chathuranga S L Rathnamalala et al. J Org Chem. .

Abstract

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 (MeORhIndz) could also be prepared by the C-H activation reaction.

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