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Conformational Dynamics of Monomer‐ versus Dimer‐like Features in a Naphthalenediimide‐Based Conjugated Cyclophane
Author(s) -
Keshri Sudhir Kumar,
Takai Atsuro,
Ishizuka Tomoya,
Kojima Takahiko,
Takeuchi Masayuki
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201914414
Subject(s) - dimer , luminescence , monomer , chemistry , enantiomer , cyclophane , dichroic glass , fluorescence , crystallography , circular dichroism , stereochemistry , photochemistry , crystal structure , materials science , organic chemistry , nanotechnology , optoelectronics , polymer , optics , physics
The design and synthesis of an enantiomeric pair of 1,8‐diethynylanthracene‐bridged naphthalenediimide (NDI)‐based cyclophanes ( Cyclo‐NDI s) are reported. Each enantiomer of Cyclo‐NDI exhibits a circularly polarized luminescence signal with a relatively large luminescence dissymmetry factor ( g lum =±8×10 −3 ). We have further investigated the modulation of through‐space electronic communication between co‐facially oriented NDIs in a discrete Cyclo‐NDI with changes in the temperature. Tuning of the electronic communication results from the conformational transformation of monomer‐ versus dimer‐like features of Cyclo‐NDI , as confirmed by UV/Vis, fluorescence, circular dichroic, and NMR spectroscopic analysis. The temperature‐dependent optical response in the Cyclo‐NDI through the conformational transformation could be utilized as a highly sensitive and reversible optical thermometer in a wide temperature range (100 to −80 °C).