Synlett
DOI: 10.1055/s-0036-1589503
letter
© Georg Thieme Verlag Stuttgart · New York

Iptycene-Containing Azaacenes with Tunable Luminescence

A. Lennart Schleper §, Constantin-Christian A. Voll §, Jens U. Engelhart, Timothy M. Swager*
  • Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge MA, 02139, USA   Email: tswager@mit.edu
Financial 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
Further Information

Publication History

Received: 05 April 2017

Accepted after revision: 15 May 2017

Publication Date:
19 July 2017 (eFirst)

§ These authors contributed equally

Abstract

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.

Supporting Information