Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 28, Issue 65, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202202922
Keywords
Chirality; circularly polarized luminescence; density functional calculations; helicene
Categories
Funding
- Cooperative Research Program of Network Joint Research Center for Materials and Devices: Dynamic Alliance for Open Innovation Bridging Human, Environment and Materials [20K05467]
- [20203034]
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A study investigated the chiral properties of a compound with organic molecules and enantiomeric structures, revealing that the oxidation of a phosphino group to a phosphine oxide induces a circularly polarized luminescence (CPL) response. The phosphine oxide showed a better CPL response, possibly due to structural changes in the interior of the helicene helix.
Small chiral organic molecules with CD properties are in high demanded due to their potential use in promising electronic and biological applications. Herein, we reveal a system in which the oxidation of a phosphino group to the corresponding phosphine oxide on the inner rim of a helicene derivative induces a CPL response. Laterally pi-extended 7,8-dihydro[5]helicenes bearing phosphine and phosphine oxide groups on their inner helical rims (i. e., the C1 position) were synthesized, and their helical structures were unambiguously determined by X-ray crystallography. The photophysical (UV/visible and emission) and chiroptical properties of these compounds were investigated in various solvents. Despite their structural similarities, phosphine oxide showed a significantly better CPL response than phosphine, with a high dissymmetry factor for emission (|g(lum)|=(1.3-1.9)x10(-3)) that can be attributed to structural changes in the interior of the helicene helix.
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