Chiroptical Amplification of [7]‐Helicene Nanographene by Additional Helical Chirality

Abstract Nanographenes have captivated scientific interest since the pioneering discovery of graphene. Recently, attention has shifted towards exploring chiral and nonplanar nanographenes, for their distinct optical, chiroptical, and electronic properties. Despite the growing acceptance of helicenes, the research on inducing helical chirality on π‐extended derivatives to boost chiroptical properties remains unattended. In our study, we introduce a new π‐extended [7]‐helicene resulting from the condensation of diamines with 3,6‐dibromophenanthrene‐9,10‐dione, complemented by two hexabenzocoronene arms in the periphery. Notably, the nanographene containing binaphtho‐[1,4]diazocine, compared to the corresponding phenazine, exhibits a remarkable average 2.5, 5, and 10‐fold enhancements in quantum yield, dissymmetry factor, and brightness, respectively, when measured in five different solvents. These improvements underscore the significance of the induced helical chirality by the antiaromatic binaphtho‐[1,4]diazocine in influencing the chiroptical properties of the helical nanographene. Our research represents a significant stride toward unlocking the potential of π‐extended helicenes and lays the groundwork for further exploration in designing and synthesizing new chiral nanomaterials.

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Publication Details

Journal
Angewandte Chemie
Published
2024-12-06
DOI
https://doi.org/10.1002/ange.202420767
Citations
1
Primary Topic
Synthesis and Properties of Aromatic Compounds
Type
article
Field-Weighted Citation Impact
0.25
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article

Chiroptical Amplification of [7]‐Helicene Nanographene by Additional Helical Chirality

Sangram D. Dongre, Ashok Badrinarayan Jadhav, Jatish Kumar, Geethu Venugopal et al.
1 citations
Angewandte Chemie
Synthesis and Properties of Aromatic Compounds
0.25
article

Chiroptical Amplification of [7]‐Helicene Nanographene by Additional Helical Chirality

Sangram D. Dongre, Ashok Badrinarayan Jadhav, Jatish Kumar, Geethu Venugopal, Sukumaran Santhosh Babu, V. Ravi Kumar
article en
1 citations

Abstract

Abstract Nanographenes have captivated scientific interest since the pioneering discovery of graphene. Recently, attention has shifted towards exploring chiral and nonplanar nanographenes, for their distinct optical, chiroptical, and electronic properties. Despite the growing acceptance of helicenes, the research on inducing helical chirality on π‐extended derivatives to boost chiroptical properties remains unattended. In our study, we introduce a new π‐extended [7]‐helicene resulting from the condensation of diamines with 3,6‐dibromophenanthrene‐9,10‐dione, complemented by two hexabenzocoronene arms in the periphery. Notably, the nanographene containing binaphtho‐[1,4]diazocine, compared to the corresponding phenazine, exhibits a remarkable average 2.5, 5, and 10‐fold enhancements in quantum yield, dissymmetry factor, and brightness, respectively, when measured in five different solvents. These improvements underscore the significance of the induced helical chirality by the antiaromatic binaphtho‐[1,4]diazocine in influencing the chiroptical properties of the helical nanographene. Our research represents a significant stride toward unlocking the potential of π‐extended helicenes and lays the groundwork for further exploration in designing and synthesizing new chiral nanomaterials.

Angewandte ChemieVol. 137(6)
National Chemical Laboratory (IN), Indian Institute of Science Education and Research, Tirupati (IN), Academy of Scientific and Innovative Research (IN)
Openalex Percentile: Top 46%
Synthesis and Properties of Aromatic Compounds
0.25
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