Chengshuo Shen1, Monika Srebro-Hooper2, Marion Jean3, Nicolas Vanthuyne3, Loïc Toupet1, J A Gareth Williams4, Alexis R Torres5, Adrian J Riives5, Gilles Muller5, Jochen Autschbach6, Jeanne Crassous1. 1. Institut des Sciences Chimiques de Rennes, UMR 6226, Institut de Physique de Rennes, UMR 6251, Campus de Beaulieu, CNRS-Université de Rennes 1, 35042, Rennes Cedex, France. 2. Faculty of Chemistry, Jagiellonian University, R. Ingardena 3, 30-060, Krakow, Poland. 3. Aix Marseille University, CNRS, Centrale Marseille, iSm2, Marseille, France. 4. Department of Chemistry, University of Durham, Durham, DH1 3LE, UK. 5. Department of Chemistry, San José State University, San José, CA, 95192-0101, USA. 6. Department of Chemistry, University at Buffalo - State University of New York, Buffalo, NY, 14260, USA.
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 ).
class="Chemical">Four members oclass="Chemical">n class="Chemical">f 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 ofboron 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 ).
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