Indolizine-Cyanine Dyes: Near Infrared Emissive Cyanine Dyes with Increased Stokes Shifts
- Award ID(s):
- 1632825
- PAR ID:
- 10092580
- Date Published:
- Journal Name:
- The Journal of Organic Chemistry
- Volume:
- 84
- Issue:
- 2
- ISSN:
- 0022-3263
- Page Range / eLocation ID:
- 687 to 697
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
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null (Ed.)We report a significant Stokes shift enhancement in near-infrared fluorescing cyanines as a result of C4′-substitution with cyclic or acyclic amines. Based on a combined experimental and density functional study, a simple strategy for optimizing the Stokes shift is proposed. By tuning the relative energies of cyanine-like and bis-dipolar conformers, differing in the rotational angle of the amine substituent, it is possible to develop molecules that undergo conformational change upon excitation, resulting in a predictable Stokes shift.more » « less
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