Journal
CHEMICAL SCIENCE
Volume 12, Issue 30, Pages 10150-10158Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1sc02718b
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Funding
- Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) [230408635, 434040413, INST 40/467-1 FUGG, INST 39/1081-1 FUGG]
- state of Baden-Wurttemberg through bwHPC
- CEA, SCBM
- Labex CHARMMMAT [ANR-11-LABX-0039]
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This study presents a strategy for the synthesis of enantiopure nanohoops with high fluorescence quantum yields and circularly polarized luminescence properties through chiral derivatization. Due to their strained structures, the DBP[n]CPPs do not racemize at room temperature, as supported by high calculated isomerization barriers. X-ray crystallographic investigations and DFT calculations provide insights into the build-up of strain energy during the synthetic transformations.
Strained conjugated nanohoops are attractive synthetic targets due to the bending of their pi-system, which leads to intriguing optoelectronic properties, among others. By incorporating non-mirror-symmetric aromatic panels, chiral nanohoops can be obtained. We herein present a strategy to enantiopure nanohoops by racemic resolution through chiral derivatization of diketone-embedded hoops. The resulting diketo[n]CPPs (n = 6, 7) contain two stereogenic carbon atoms each and possess high fluorescence quantum yields paired with circularly polarized luminescence. These are versatile precursors to chiral dibenzo[a,e]pentalene-based nanohoops DBP[n]CPPs with antiaromatic character and ambipolar electrochemical behavior. Due to their strained structures the DBP[n]CPPs do not racemize at room temperature, which is supported by high calculated isomerization barriers. X-ray crystallographic investigations on the DBP[n]CPPs and their precursors as well as DFT calculations provide insight into the build-up of strain energy during the synthetic transformations.
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