Indolizine-Cyanine Dyes: Near Infrared Emissive Cyanine Dyes with Increased Stokes Shifts

Jacqueline Gayton, Shane A. Autry, William Meador, Sean R. Parkin, Glake Alton Hill, Nathan I. Hammer, Jared H. Delcamp

Research output: Contribution to journalArticlepeer-review

43 Scopus citations


Molecular engineering strategies designed to red-shift cyanine dye absorptions and emissions further into the near-infrared (NIR) spectral region are explored. Through the use of a novel donor group, indolizine, with varying cyanine bridge lengths, dye absorptions and emissions, were shifted deeper into the NIR region than common indoline-cyanines. Stokes shifts resulting from intramolecular steric interactions of up to ?60 nm in many cases were observed and explained computationally. Molecular brightnesses of up to 5800 deep into the NIR region were observed. Structure-property relationships are explored for the six indolizine-cyanine dyes with varying cyanine bridge length and indolizine substituents showing broad absorption and emission tunability. The dyes are characterized by crystallography, and the photophysical properties are probed by varying solvent for absorption and emission studies. Computational data show involvement of the entire indolizine ?-system during light absorption, which suggests these systems can be tunable even further into the NIR region through select derivatizations.

Original languageEnglish
Pages (from-to)687-697
Number of pages11
JournalJournal of Organic Chemistry
Issue number2
StatePublished - Jan 18 2019

Bibliographical note

Publisher Copyright:
© 2018 American Chemical Society.

ASJC Scopus subject areas

  • Organic Chemistry


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