The Synthesis, X-ray Structure Analysis, and Photophysical Characterization of 4-[(<em>Eem>)-2-(4-Carboxyphenyl)diazenyl]-morpholine
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- 作者：Mathew Johnson ; Michael Galbreath ; Frank R. Fronczek and Ralph Isovitsch
- 刊名：Journal of Heterocyclic Chemistry
- 出版年：2016
- 出版时间：November 2016
- 年：2016
- 卷：53
- 期：6
- 页码：2091-2095
- 全文大小：473K
- ISSN：1943-5193
文摘
erm3">4-[(<em>Eem>)-2-(4-Carboxyphenyl)diazenyl]-morpholine (ef="#jhet2494-eo-0001" rel="references:#jhet2494-eo-0001">) was prepared in 33% yield from a erm4">coupling reaction between ey.com/namespaces/wiley" xmlns:cr="urn://wiley-online-library/content/render" xmlns:mml="http://www.w3.org/1998/Math/MathML" id="jhet2494-eo-2001">erm1 TH_term3">morpholine and the diazonium ion formed from ey.com/namespaces/wiley" xmlns:cr="urn://wiley-online-library/content/render" xmlns:mml="http://www.w3.org/1998/Math/MathML" id="jhet2494-eo-2002">erm2 TH_term3">4-aminobenzoic acid. X-ray structural analysis of ef="#jhet2494-eo-0001" rel="references:#jhet2494-eo-0001"> yielded two important insights into its structure: the geometry of the N―N double bond and the partial delocalization across the linear triazene moiety. The absorption spectra of ef="#jhet2494-eo-0001" rel="references:#jhet2494-eo-0001"> in dilute acetonitrile and 2-methyltetrahydrofuran solutions both featured an intense (<em>εem> ≈ 20,000 M−1cm−1) band centered at 320–324 nm that was assigned as a mixture of π → π* and n → π* transitions. Emission was observed at 383 and 379 nm from dilute acetonitrile and 2-methyltetrahydrofuran solutions of ef="#jhet2494-eo-0001" rel="references:#jhet2494-eo-0001">, respectively, with the latter being red-shifted to 439 nm at 77 K. Emission lifetime data for compound ef="#jhet2494-eo-0001" rel="references:#jhet2494-eo-0001"> provided evidence that the emission was a mixture of two excited state transitions.