%0 Journal Article %1 Tian_2023 %A Tian, Xiaoqi %A Shoyama, Kazutaka %A Mahlmeister, Bernhard %A Brust, Felix %A Stolte, Matthias %A Würthner, Frank %D 2023 %I American Chemical Society (ACS) %J J. Am. Chem. Soc. %K myown %R 10.1021/jacs.3c03441 %T Naphthalimide-Annulated nHelicenes: Red Circularly Polarized Light Emitters %U https://doi.org/10.1021%2Fjacs.3c03441 %X Two nheliceno-bis(naphthalimides) 1 and 2 (n = 5 and 6, respectively) where two electron-accepting naphthalimide moieties are attached at both ends of helicene core were synthesized by effective two-step strategy, and their enantiomers could be resolved by chiral stationary-phase high-performance liquid chromatography (HPLC). The single-crystal X-ray diffraction analysis of enantiopure fractions of 1 and 2 confirmed their helical structure, and together with experimental and calculated circular dichroism (CD) spectra, the absolute configuration was unambiguously assigned. Both 1 and 2 exhibit high molar extinction coefficients for the S0–S1 transition and high fluorescence quantum yields (73% for 1 and 69% for 2), both being outstanding for helicene derivatives. The red circularly polarized luminescence (CPL) emission up to 615 nm for 2 with CPL brightness (BCPL) up to 66.5 M–1 cm–1 demonstrates its potential for applications in chiral optoelectronics. Time-dependent density functional theory (TD-DFT) calculations unambiguously showed that the large transition magnetic dipole moment |m| of 2 is responsible for its high absorbance dissymmetry (gabs) and luminescence dissymmetry (glum) factor.

@article{Tian_2023, abstract = {Two [n]heliceno-bis(naphthalimides) 1 and 2 (n = 5 and 6, respectively) where two electron-accepting naphthalimide moieties are attached at both ends of helicene core were synthesized by effective two-step strategy, and their enantiomers could be resolved by chiral stationary-phase high-performance liquid chromatography (HPLC). The single-crystal X-ray diffraction analysis of enantiopure fractions of 1 and 2 confirmed their helical structure, and together with experimental and calculated circular dichroism (CD) spectra, the absolute configuration was unambiguously assigned. Both 1 and 2 exhibit high molar extinction coefficients for the S0–S1 transition and high fluorescence quantum yields (73% for 1 and 69% for 2), both being outstanding for helicene derivatives. The red circularly polarized luminescence (CPL) emission up to 615 nm for 2 with CPL brightness (BCPL) up to 66.5 M–1 cm–1 demonstrates its potential for applications in chiral optoelectronics. Time-dependent density functional theory (TD-DFT) calculations unambiguously showed that the large transition magnetic dipole moment |m| of 2 is responsible for its high absorbance dissymmetry (gabs) and luminescence dissymmetry (glum) factor.}, added-at = {2023-05-03T10:24:49.000+0200}, author = {Tian, Xiaoqi and Shoyama, Kazutaka and Mahlmeister, Bernhard and Brust, Felix and Stolte, Matthias and Würthner, Frank}, biburl = {https://www.bibsonomy.org/bibtex/2af19f832ddcf095de55937f043e7503f/wuerthner_group}, doi = {10.1021/jacs.3c03441}, interhash = {a329fea5e166bfa004335d1a8b53aa55}, intrahash = {af19f832ddcf095de55937f043e7503f}, journal = {J. Am. Chem. Soc.}, keywords = {myown}, month = apr, publisher = {American Chemical Society (ACS)}, timestamp = {2023-05-23T13:14:33.000+0200}, title = {Naphthalimide-Annulated [n]Helicenes: Red Circularly Polarized Light Emitters}, url = {https://doi.org/10.1021%2Fjacs.3c03441}, year = 2023 }