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Conformational Control and Photophysical Properties of Methylene‐Tethered Bis[(naphthalene‐2‐yl)vinyl]benzenes
Author(s) -
Watanabe Shoya,
Yamanishi Katsunori,
Tsuji Hayato
Publication year - 2019
Publication title -
chemphotochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.13
H-Index - 18
ISSN - 2367-0932
DOI - 10.1002/cptc.201900145
Subject(s) - bathochromic shift , naphthalene , conformational isomerism , photochemistry , chemistry , absorption (acoustics) , fluorescence , spectroscopy , benzene , absorption spectroscopy , methylene , materials science , medicinal chemistry , organic chemistry , molecule , physics , quantum mechanics , composite material
We have synthesized and isolated three planar dibenzo‐fused oligo(phenylenevinylene) isomers ( l ‐DBCOPV2 , u ‐DBCOPV2 , and b ‐DBCOPV2 ), which serve as model compounds for rotational conformers of bis[(naphthalene‐2‐yl)vinyl]benzene. Their photophysical properties were examined by UV/Vis absorption and emission spectroscopy, revealing that their emission colors changed from sky‐blue to green depending on the conformation. We have also measured their fluorescence lifetimes and carried out DFT calculations. These investigations revealed a more detailed conformation‐dependent character for l ‐DBCOPV2 , u ‐DBCOPV2 , and b ‐DBCOPV2 : The UV/Vis absorption and emission bands showed bathochromic shifts that increased in the order l ‐DBCOPV2 < u ‐DBCOPV2 < b ‐DBCOPV2 , whereas the extinction coefficients of the absorption decreased in the same order, suggesting a difference in the orbital interactions between the divinylbenzene core and the naphthalene components.