Impact of aromatic ether substituents on chiroptical properties in BINOL-based systems
Abstract
Chiral organic emitters require a detailed understanding of structure-(chiro)optical property relationships. Herein, we design and synthesise a series of axially chiral BINOL-based enantiomers functionalized with aromatic ether substituents of increasing steric size and electronic extent, aiming to investigate how aromatic size and rigidity influence ground-and excited-state chiroptical responses. We started with a simple phenyl unit, followed by an extended naphthyl group. In contrast to sizedependent enhancement, the phenyl-and naphthyl-substituted derivatives exhibit similar absorption dissymmetry factors (gabs) across the 320-360 nm region, which indicates that linear p-extension alone does not significantly alter the chiroptical response. Therefore, we designed a more rigid structure using bi-naphthyl, with two covalently interconnected naphthyl units, which further restricted intramolecular rotation. As a result, an increase in gabs was observed. This result signifies the crucial role of conformational rigidity and suppression of intramolecular rotation in governing chiroptical amplification.
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BibTeX
@article{thakur2026impact,
title = {{Impact of aromatic ether substituents on chiroptical properties in BINOL-based systems}},
author = {Diksha Thakur and Biswaranjan Sahu and Wijak Yospanya and Reiko Oda and Sivakumar Vaidyanathan},
journal = {Journal of Materials Chemistry C},
year = {2026},
month = aug,
doi = {10.1039/d6tc01901c},
url = {https://hal.science/hal-05794511v1},
note = {CC BY 4.0},
}
RIS
TY - JOUR
TI - Impact of aromatic ether substituents on chiroptical properties in BINOL-based systems
AU - Diksha Thakur
AU - Biswaranjan Sahu
AU - Wijak Yospanya
AU - Reiko Oda
AU - Sivakumar Vaidyanathan
PY - 2026
DA - 2026/08/19
JO - Journal of Materials Chemistry C
DO - 10.1039/d6tc01901c
UR - https://hal.science/hal-05794511v1
AB - Chiral organic emitters require a detailed understanding of structure-(chiro)optical property relationships. Herein, we design and synthesise a series of axially chiral BINOL-based enantiomers functionalized with aromatic ether substituents of increasing steric size and electronic extent, aiming to investigate how aromatic size and rigidity influence ground-and excited-state chiroptical responses. We started with a simple phenyl unit, followed by an extended naphthyl group. In contrast to sizedependent enhancement, the phenyl-and naphthyl-substituted derivatives exhibit similar absorption dissymmetry factors (gabs) across the 320-360 nm region, which indicates that linear p-extension alone does not significantly alter the chiroptical response. Therefore, we designed a more rigid structure using bi-naphthyl, with two covalently interconnected naphthyl units, which further restricted intramolecular rotation. As a result, an increase in gabs was observed. This result signifies the crucial role of conformational rigidity and suppression of intramolecular rotation in governing chiroptical amplification.
SN - 2050-7526
SN - 2050-7534
ER -