Journal article
Synthesis and characterization of chiral and achiral diamines containing one or two BODIPY molecules
New journal of chemistry, Vol.41(23), pp.14370-14378
2017
Handle:
https://hdl.handle.net/2376/115629
Abstract
The synthesis and characterization of one or two BODIPY fragments appended to four new chiral and one new achiral diamines is described. All of the examined BODIPY-appended diamines exhibit a quasireversible-irreversible reduction, with two reductions (separated by about 100 mV) observed in the case of diamines containing two BODIPY molecules. Only the BODIPY-appended ortho-phenylenediamines did not fluoresce under UV light. Computational analysis showed that the absence of fluorescence of the BODIPY-appended ortho-phenylenediamines is likely due to intramolecular quenching of the excited state electron within the phenylenediamine ligand. Computational analysis also showed that the incorporation of a BODIPY molecule greatly reduces the basicity of the amine center, by about 10–14 pKa units. The BODIPY moiety was found to be more electron withdrawing than a tosyl and a pentafluorophenyl group, suggesting why excess metals are needed in heavy metal sensor applications (heteroatom-appended BODIPYs = poor ligands). An improved procedure for the scalable synthesis (greater than three grams) of 8-methanethio-BODIPY, a common starting material for the generation of heteroatom-appended BODIPY molecules, is also described.
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Details
- Title
- Synthesis and characterization of chiral and achiral diamines containing one or two BODIPY molecules
- Creators
- Nicholas R Treich - Department of Chemistry, Washington State University, Pullman, USAJacob D Wimpenny - Department of Chemistry, Washington State University, Pullman, USAIan A Kieffer - Department of Chemistry, Washington State University, Pullman, USAZachariah M Heiden - Department of Chemistry, Washington State University, Pullman, USA
- Publication Details
- New journal of chemistry, Vol.41(23), pp.14370-14378
- Academic Unit
- Chemistry, Department of
- Identifiers
- 99900548334201842
- Language
- English
- Resource Type
- Journal article