Divergent Synthesis of Double Heterohelicenes as Strong Chiral Double Hydrogen-Bonding Donors
Zuobang Sun, Chunyang Yu, Ningjin Zhang, Lingling Li, Yang Jiao, Thiruvengadam Palani, Dongqing Wu, Fan Zhang
Abstract
We developed a very efficient and expandable divergent approach initiated by a direct electrophilic borylation at phenyl rings to synthesize a series of double heterohelicenes. Their π-extended structures with pristine zigzag nitrogen (N)–boron (B)–nitrogen (N) edges offer them substantial physical properties and strong double hydrogen-bond donating capability. The isolated (P,P) and (M,M) enantiomers exhibit circularly polarized luminescence in response to hydrogen-bonding interactions.
Topics & Concepts
ChemistryElectrophileDouble bondHydrogen bondBoronBorylationZigzagNitrogenEnantiomerHydrogenLuminescenceStereochemistryCrystallographyCatalysisMoleculePolymer chemistryOrganic chemistryOptoelectronicsMaterials scienceAlkylGeometryMathematicsArylSynthesis and Properties of Aromatic CompoundsOrganoboron and organosilicon chemistrySynthesis and characterization of novel inorganic/organometallic compounds