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We report emerging circularly polarized luminescence (CPL) at 4 f- 4 f  transitions when lanthanide (Eu III  and Tb III ) tris(β-diketonate) embedded to cellulose triacetate ( CTA ), cellulose acetate butyrate ( CABu ),  D -/ L -glucose pentamethyl esters (  D - /  L -Glu ), and  D -/ L -arabinose tetramethyl esters (  D - /  L -Ara ) are in film states. Herein, 6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionate (fod) and 2,2,6,6-tetramethyl-3,5-heptanedione (dpm) were chosen as the β-diketonates. The  g  lum  value of Eu(fod) 3  in  CABu  are +0.0671 at 593 nm ( 5D    0→    7F 1 ) and −0.0059 at 613 nm ( 5D    0→    7F 2 ), respectively, while those in  CTA  are +0.0463 and −0.0040 at these transitions, respectively. The  g  lum  value of Tb(fod) 3  in  CABu  are −0.0029 at 490 nm ( 5D    4→    7F 6 ), +0.0078 at 540 nm ( 5D    4→    7F 5 ), and −0.0018 at 552 nm ( 5D    4→    7F 5 ), respectively, while those in  CTA  are −0.0053, +0.0037, and −0.0059 at these transitions, respectively.   D - /  L -Glu  and   D - /  L -Ara  induced weaker  g  lum  values at 4 f- 4 f  transitions of Eu(fod) 3 , Tb(fod) 3 , and Tb(dpm) 3 . For comparison, Tb(dpm) 3  in α-pinene showed clear CPL characteristics, though Eu(dpm) 3  did not. A surplus charge neutralization hypothesis was applied to the origin of attractive intermolecular interactions between the ligands and saccharides. This idea was supported from the concomitant opposite tendency in upfield  19 F-NMR and downfield  1 H-NMR chemical shifts of Eu(fod) 3  and the opposite Mulliken charges between  F -C bonds (fod) and  H -C bonds ( CTA  and   D - /  L -Glu ). An analysis of CPL excitation (CPLE) and CPL spectra suggests that (+)- and (–)-sign CPL signals of Eu III  and Tb III  at different 4 f- 4 f  transitions in the visible region are the same with the (+)-and (–)-sign exhibited by CPLE bands at high energy levels of Eu III  and Tb III  in the near-UV region.

frontiers in chemistry

Chirogenesis and Pfeiffer Effect in Optically Inactive EuIII and TbIII Tris(β-diketonate) Upon Intermolecular Chirality Transfer From Poly- and Monosaccharide Alkyl Esters and α-Pinene: Emerging Circularly Polarized Luminescence (CPL) and Circular Dichroism (CD)