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

Chathuranga S L Rathnamalala; Jacqueline N Gayton; Austin L Dorris; Shane A Autry; William Meador; Nathan I Hammer; Jared H Delcamp; Colleen N Scott

doi:10.1021/acs.joc.9b01860

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

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

Authors

Chathuranga S L Rathnamalala¹, Jacqueline N Gayton², Austin L Dorris², Shane A Autry², William Meador², Nathan I Hammer², Jared H Delcamp², Colleen N Scott¹

Affiliations

¹ Department of Chemistry, Hand Lab 1115 , Mississippi State University , Mississippi State , Mississippi 39762 , United States.
² Department of Chemistry and Biochemistry, Coulter Hall , University of Mississippi , University , Mississippi 38677 , United States.

PMID: 31479270
DOI: 10.1021/acs.joc.9b01860

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.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.