Synthesis and Stereodynamic and Emission Properties of Dissymmetric Bis-Aryl Carbazole Boranes and Identification of a CPL-Active B-C Atropisomeric Compound

Overview

Journal J Org Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2023 Jan 4

PMID 36599041

Authors

Daniel Pecorari

Emanuele Giuliani

Andrea Mazzanti

Stefano Stagni

Valentina Fiorini

Giulia Vigarani

Francesco Zinna

Gennaro Pescitelli

Michele Mancinelli

Affiliations

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Abstract

We synthesized bis-aryl carbazole borane derivatives having emissive properties and axial chirality. The resolution of a thermally stable atropisomeric pair (compound ), due to a B-C chiral axis, was achieved by chiral stationary-phase high-performance liquid chromatography (CSP-HPLC). Complete photophysical properties of all compounds were measured and simulated by time-dependent density functional theory (TD-DFT) calculations of the complete fluorescence cycle, and circularly polarized luminescence spectra were obtained for the atropisomers of compound , whose absolute configuration was derived using a TD-DFT simulation of the electronic circular dichroism (ECD) spectra.

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References

Jacquemin D, Wathelet V, Perpete E, Adamo C . Extensive TD-DFT Benchmark: Singlet-Excited States of Organic Molecules. J Chem Theory Comput. 2015; 5(9):2420-35. DOI: 10.1021/ct900298e. View

Chen C, Zheng W . Planar Chiral B-N Heteroarenes Based on [2.2]Paracyclophane as Circularly Polarized Luminescence Emitters. Org Lett. 2021; 23(14):5554-5558. DOI: 10.1021/acs.orglett.1c01924. View

Chen J, Yin X, Wang B, Zhang K, Meng G, Zhang S . Planar Chiral Organoboranes with Thermoresponsive Emission and Circularly Polarized Luminescence: Integration of Pillar[5]arenes with Boron Chemistry. Angew Chem Int Ed Engl. 2020; 59(28):11267-11272. DOI: 10.1002/anie.202001145. View

Cui Y, Liu Q, Bai D, Jia W, Tao Y, Wang S . Organoboron compounds with an 8-hydroxyquinolato chelate and its derivatives: substituent effects on structures and luminescence. Inorg Chem. 2005; 44(3):601-9. DOI: 10.1021/ic0489746. View

Sanchez-Carnerero E, Moreno F, Maroto B, Agarrabeitia A, Ortiz M, Vo B . Circularly polarized luminescence by visible-light absorption in a chiral O-BODIPY dye: unprecedented design of CPL organic molecules from achiral chromophores. J Am Chem Soc. 2014; 136(9):3346-9. PMC: 3984031. DOI: 10.1021/ja412294s. View

Jimenez J, Cerdan L, Moreno F, Maroto B, Garcia-Moreno I, Lunkley J . Chiral Organic Dyes Endowed with Circularly Polarized Laser Emission. J Phys Chem C Nanomater Interfaces. 2017; 121(9):5287-5292. PMC: 5630177. DOI: 10.1021/acs.jpcc.7b00654. View

Mazzanti A, Boffa M, Marotta E, Mancinelli M . Axial Chirality at the Boron-Carbon Bond: Synthesis, Stereodynamic Analysis, and Atropisomeric Resolution of 6-Aryl-5,6-dihydrodibenzo[][1,2]azaborinines. J Org Chem. 2019; 84(19):12253-12258. DOI: 10.1021/acs.joc.9b01550. View

Full J, Panchal S, Gotz J, Krause A, Nowak-Krol A . Modular Synthesis of Organoboron Helically Chiral Compounds: Cutouts from Extended Helices. Angew Chem Int Ed Engl. 2020; 60(8):4350-4357. PMC: 7898935. DOI: 10.1002/anie.202014138. View

Saikawa M, Nakamura T, Uchida J, Yamamura M, Nabeshima T . Synthesis of figure-of-eight helical bisBODIPY macrocycles and their chiroptical properties. Chem Commun (Camb). 2016; 52(71):10727-30. DOI: 10.1039/c6cc05439k. View

10.

Katayama T, Nakatsuka S, Hirai H, Yasuda N, Kumar J, Kawai T . Two-Step Synthesis of Boron-Fused Double Helicenes. J Am Chem Soc. 2016; 138(16):5210-3. DOI: 10.1021/jacs.6b01674. View

11.

Ray C, Sanchez-Carnerero E, Moreno F, Maroto B, Agarrabeitia A, Ortiz M . Bis(haloBODIPYs) with Labile Helicity: Valuable Simple Organic Molecules That Enable Circularly Polarized Luminescence. Chemistry. 2016; 22(26):8805-8. PMC: 5060947. DOI: 10.1002/chem.201601463. View

12.

Alam M, Chattopadhyaya M, Chakrabarti S . A critical theoretical study on the two-photon absorption properties of some selective triaryl borane-1-naphthylphenyl amine based charge transfer molecules. Phys Chem Chem Phys. 2011; 13(20):9285-92. DOI: 10.1039/c0cp02958k. View

13.

Taniguchi T, Wang J, Irle S, Yamaguchi S . TICT fluorescence of N-borylated 2,5-diarylpyrroles: a gear like dual motion in the excited state. Dalton Trans. 2012; 42(3):620-4. DOI: 10.1039/c2dt32134c. View

14.

Superchi S, Scafato P, Gorecki M, Pescitelli G . Absolute Configuration Determination by Quantum Mechanical Calculation of Chiroptical Spectra: Basics and Applications to Fungal Metabolites. Curr Med Chem. 2017; 25(2):287-320. DOI: 10.2174/0929867324666170310112009. View

15.

Sanchez-Carnerero E, Agarrabeitia A, Moreno F, Maroto B, Muller G, Ortiz M . Circularly Polarized Luminescence from Simple Organic Molecules. Chemistry. 2015; 21(39):13488-500. PMC: 4567477. DOI: 10.1002/chem.201501178. View

16.

Zinna F, Bruhn T, Guido C, Ahrens J, Broring M, Di Bari L . Circularly Polarized Luminescence from Axially Chiral BODIPY DYEmers: An Experimental and Computational Study. Chemistry. 2016; 22(45):16089-16098. DOI: 10.1002/chem.201602684. View

17.

Sun Z, Liu J, Yuan D, Zhao Z, Zhu X, Liu D . 2,2'-Diamino-6,6'-diboryl-1,1'-binaphthyl: A Versatile Building Block for Temperature-Dependent Dual Fluorescence and Switchable Circularly Polarized Luminescence. Angew Chem Int Ed Engl. 2019; 58(15):4840-4846. DOI: 10.1002/anie.201813320. View

18.

Wang J, Wang Y, Taniguchi T, Yamaguchi S, Irle S . Substituent effects on twisted internal charge transfer excited states of N-borylated carbazoles and (diphenylamino)boranes. J Phys Chem A. 2012; 116(4):1151-8. DOI: 10.1021/jp209264j. View

19.

Takaishi K, Iwachido K, Ema T . Solvent-Induced Sign Inversion of Circularly Polarized Luminescence: Control of Excimer Chirality by Hydrogen Bonding. J Am Chem Soc. 2020; 142(4):1774-1779. DOI: 10.1021/jacs.9b13184. View

20.

Qin Y, Kiburu I, Shah S, Jakle F . Luminescence tuning of organoboron quinolates through substituent variation at the 5-position of the quinolato moiety. Org Lett. 2006; 8(23):5227-30. DOI: 10.1021/ol0619664. View