Dataset for Green-Tuning of (Chir)Optical Properties for Axially-Chiral Boramidines

The integration of boron into π-conjugated systems is a reliable approach to enhance photophysical properties. In this context, boramidines have emerged as a promising class of fluorophores. Herein, the design, synthesis, and chiroptical properties of novel axially chiral isoquinoline-derived boramidines is reported. Thanks to metal-catalyzed cross-coupling allied with atroposelective C-H arylation strategies or chiral stationary phase HPLC resolution, enantioenriched boramidines 1 and 2 are afforded (ee 90-99%). Comparing with more classical boramidines, investigations reveal (i) bathochromic absorption shifts in the UV-Vis region (>50 nm) and (ii) emission maxima now in the green and cyan domains, along with fluorescence quantum yields reaching 70% in N2-saturated environments. Chiroptical measurements demonstrate well-defined electronic circular dichroism (ECD) spectra and circularly polarized luminescence (CPL) signals with |glum| values up to 2·10⁻³.

Organizational unit: Laboratory of Professor Jérôme Lacour

Type: Dataset

DOI: 10.26037/yareta:2u5mivz4zndrfbom3gprrcvllm

License: Creative Commons Attribution 4.0 International

Keywords: : Axial Chirality, Atroposelective Synthesis, Boramidine, Circular Dichroism, Circularly Polarized Luminescence

Publication date

26/03/2025

Retention date24/03/2035

Access levelPublic

SensitivityBlue

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Contributors

Arrico, Lorenzo

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        <datacite:title>Dataset for Green-Tuning of (Chir)Optical Properties for Axially-Chiral Boramidines</datacite:title>
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    <datacite:publisher>Université de Genève, Yareta</datacite:publisher>
    <datacite:publicationYear>2025</datacite:publicationYear>
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        <datacite:date dateType="Issued">2025-03-26T00:00:00Z</datacite:date>
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        <datacite:date dateType="Updated">2025-04-02T13:57:40.815119Z</datacite:date>
        <datacite:date dateType="Accepted">2025-04-02T13:57:40.282459315Z</datacite:date>
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        <datacite:description descriptionType="Abstract" xml:lang="en">The integration of boron into π-conjugated systems is a reliable approach to enhance photophysical properties. In this context, boramidines have emerged as a promising class of fluorophores. Herein, the design, synthesis, and chiroptical properties of novel axially chiral isoquinoline-derived boramidines is reported. Thanks to metal-catalyzed cross-coupling allied with atroposelective C-H arylation strategies or chiral stationary phase HPLC resolution, enantioenriched boramidines 1 and 2 are afforded (ee 90-99%). Comparing with more classical boramidines, investigations reveal (i) bathochromic absorption shifts in the UV-Vis region (&gt;50 nm) and (ii) emission maxima now in the green and cyan domains, along with fluorescence quantum yields reaching 70% in N2-saturated environments. Chiroptical measurements demonstrate well-defined electronic circular dichroism (ECD) spectra and circularly polarized luminescence (CPL) signals with |glum| values up to 2·10⁻³.</datacite:description>
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