Iptycene-Containing Azaacenes with Tunable Luminescence
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s1-ln266658691928138751-1939656818Hwf590289294IdV118460964326665869PDF_HI0001.pdf
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5.24 MB
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Author(s)
Schleper, Alexander Lennart
Voll, Constantin-Chri Alexander
Engelhart, Jens
Swager, Timothy M
Date Issued
December 2017
Journal
Synlett
Publisher
Thieme Publishing Group
Citation
Schleper, A., et al. “Iptycene-Containing Azaacenes with Tunable Luminescence.” Synlett, vol. 28, no. 20, Dec. 2017, pp. 2783–89.
Version
Original manuscript
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. Keywords: N-heteroiptycene - Suzuki–Miyaura cross-coupling - Sonogashira coupling - pyrazinoquinoxaline - luminescence
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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Creative Commons Attribution-Noncommercial-Share Alike
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DOI of Published Version
https://doi.org/10.1055/s-0036-1589503
