Iptycene-Containing Azaacenes with Tunable LuminescenceFinancial support was provided through the Airforce Office of Scientific Research, a Cusanuswerk scholarship of ALS, a MITei fellowship of CCAV sponsored by Eni S.p.A., and the German Research Foundation (DFG) of JUE
Received: 05 April 2017
Accepted after revision: 15 May 2017
19 July 2017 (eFirst)
§ These authors contributed equally
An optimized route toward iptycene-capped, p-dibromo-quinoxalinophenazine was developed, increasing the yield significantly from literature procedures. New iptycene-containing symmetrical azaacenes were synthesized from this intermediate using Suzuki–Miyaura cross-coupling, and their photophysical properties were evaluated. Tuning the substituents allows modulating emission wavelengths across the visible spectrum. Substitution with 3-methoxy-2-methylthiophene exhibits a quantum yield of 35%. The (triisopropylsilyl)acetylene product has a quantum yield of 38% and serves as a model compound for the synthesis of polymers based on this electrooptically active molecular motif.