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.

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: Dec 1, 2017
• 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
• Public URL: https://durham-repository.worktribe.com/output/1382590