Litcius/Paper detail

Small Figure‐Eight Luminophores: Double‐Twisted Tethered Cyclic Binaphthyls Boost Circularly Polarized Luminescence

Yuki Nojima, Masashi Hasegawa, Nobuyuki Hara, Yoshitane Imai, Yasuhiro Mazaki

2021Chemistry - A European Journal58 citationsDOI

Abstract

Abstract Double‐twisted cyclic binaphthyls, in which two naphthalenes are tethered by ‐O(CH 2 ) n O‐ linkage ( n =1–3), have been synthesized. X‐ray analyses and DFT calculations revealed a tightly constrained stereogenic figure‐eight geometry. Tethering of two naphthalenes by short linkage forces a small dihedral angle, and the cyclic binaphthyls with short tether ( n =1, 2) exhibit remarkable boosting of the g lum value (1.0–1.6×10 −2 ) in circularly polarized luminescence (CPL) and unusual g lum / g abs ratios (0.93–1.3). These experimental high | g lum | values are in accord with the results of excited state TD‐DFT calculations, which show transannular interactions and that consequent extensive delocalization occurs throughout the figure‐eight π‐core. As a result, the present figure‐eight luminophore promote the elongation of the magnetic transition dipole moment that results in significant increases in g lum values.

Topics & Concepts

Dihedral angleLuminophoreLuminescenceDelocalized electronExcited stateStereocenterCrystallographyTransition dipole momentDipoleChemistryStereochemistryPhysicsAtomic physicsEnantioselective synthesisOpticsMoleculeCatalysisHydrogen bondBiochemistryOrganic chemistrySynthesis and Properties of Aromatic CompoundsLuminescence and Fluorescent MaterialsOrganoboron and organosilicon chemistry