Synthesis and Chiroptical Properties of Biscarbazole-Embedded Diaza[7]helicenes

In this study, we report the synthesis and chiroptical properties of biscarbazole-embedded diaza[7]helicenes. Although the classical photocyclization pathway was unsuccessful, the strategic introduction of a bromo group successfully yielded the desired helical compounds. Interestingly, using methoxy groups instead of bromo groups led to the formation of an unusual degraded product during photocyclization. The synthesized molecules were resolved into their enantiomers, and their chiroptical properties were investigated by using steady-state absorption and emission spectroscopy. Additionally, the excited-state dynamics were examined through time-resolved fluorescence decay measurements. Quantum chemical calculations were performed to rationalize the observed optical properties.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-04-14
DOI
https://doi.org/10.1021/acs.joc.5c00085
Citations
2
Primary Topic
Synthesis and Properties of Aromatic Compounds
Type
article
Field-Weighted Citation Impact
1.87

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article

Synthesis and Chiroptical Properties of Biscarbazole-Embedded Diaza[7]helicenes

Ashutosh V. Bedekar, Gourav M. Upadhyay, Asim Kumar Swain, Esha H. Bhalodi et al.
2 citations
The Journal of Organic Chemistry
Synthesis and Properties of Aromatic Compounds
1.87
article

Synthesis and Chiroptical Properties of Biscarbazole-Embedded Diaza[7]helicenes

Ashutosh V. Bedekar, Gourav M. Upadhyay, Asim Kumar Swain, Esha H. Bhalodi, Prince Ravat
article en
2 citations

Abstract

In this study, we report the synthesis and chiroptical properties of biscarbazole-embedded diaza[7]helicenes. Although the classical photocyclization pathway was unsuccessful, the strategic introduction of a bromo group successfully yielded the desired helical compounds. Interestingly, using methoxy groups instead of bromo groups led to the formation of an unusual degraded product during photocyclization. The synthesized molecules were resolved into their enantiomers, and their chiroptical properties were investigated by using steady-state absorption and emission spectroscopy. Additionally, the excited-state dynamics were examined through time-resolved fluorescence decay measurements. Quantum chemical calculations were performed to rationalize the observed optical properties.

The Journal of Organic ChemistryVol. 90(16)
Maharaja Sayajirao University of Baroda (IN), University of Würzburg (DE)
Science and Engineering Research Board
Openalex Percentile: Top 16%
Synthesis and Properties of Aromatic Compounds
1.87
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