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Synthesis and Chiroptical Properties of Hexa-, Octa-, and Decaazaborahelicenes: Influence of Helicene Size and of the Number of Boron Atoms

Shen, C.; Srebro-Hooper, M.; Jean, M.; Vanthuyne, N.; Toupet, L.; Williams, J.A.G.; Torres, A.R.; Riives, A.J.; Muller, G.; Autschbach, J.; Crassous, J.

Synthesis and Chiroptical Properties of Hexa-, Octa-, and Decaazaborahelicenes: Influence of Helicene Size and of the Number of Boron Atoms Thumbnail


Authors

C. Shen

M. Srebro-Hooper

M. Jean

N. Vanthuyne

L. Toupet

A.R. Torres

A.J. Riives

G. Muller

J. Autschbach

J. Crassous



Abstract

Four members of a new class of cycloborylated hexa-, octa-, and deca-helicenes (1 a–d) have been prepared in enantiopure form, along with two cycloplatinated deca-helicenes (1 d′, 1 d1), further extending the family of cycloplatinated hexa- and octa-helicenes reported previously. The azabora[n]helicenes display intense electronic circular dichroism and large optical rotations; the dependence of the optical activity on the size of the helix (n=6, 8, 10) and the number of boron atoms (1 or 2) has been examined in detail both experimentally and theoretically. The photophysical properties (nonpolarized and circularly polarized luminescence) of these new fluorescent organic helicenes have been measured and compared with the corresponding organometallic phosphorescent cycloplatinated derivatives (1 a1–d1).

Citation

Shen, C., Srebro-Hooper, M., Jean, M., Vanthuyne, N., Toupet, L., Williams, J., …Crassous, J. (2017). Synthesis and Chiroptical Properties of Hexa-, Octa-, and Decaazaborahelicenes: Influence of Helicene Size and of the Number of Boron Atoms. Chemistry - A European Journal, 23(2), 407-418. https://doi.org/10.1002/chem.201604398

Journal Article Type Article
Acceptance Date Oct 18, 2016
Online Publication Date Dec 1, 2016
Publication Date Jan 5, 2017
Deposit Date Mar 17, 2017
Publicly Available Date Mar 29, 2024
Journal Chemistry - A European Journal
Print ISSN 0947-6539
Electronic ISSN 1521-3765
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 23
Issue 2
Pages 407-418
DOI https://doi.org/10.1002/chem.201604398

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Copyright Statement
This is the peer reviewed version of the following article: C. Shen, M. Srebro-Hooper, M. Jean, N. Vanthuyne, L. Toupet, J. A. G. Williams, A. R. Torres, A. J. Riives, G. Muller, J. Autschbach, J. Crassous, Chemistry - A European Journal 2017, 23(2): 407-418, which has been published in final form at https://doi.org/10.1002/chem.201604398. This article may be used for non-commercial purposes in accordance With Wiley-VCH Terms and Conditions for self-archiving.





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