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Multichromophore arrays of dibenzotetraaza[14]annulene: a promising platform for bioorganic chemistry†
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2018-07-11 00:00:00 , DOI: 10.1039/c8ob01078a Krzysztof M. Zwoliński 1, 2, 3, 4 , Julita Eilmes 1, 2, 3, 4
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2018-07-11 00:00:00 , DOI: 10.1039/c8ob01078a Krzysztof M. Zwoliński 1, 2, 3, 4 , Julita Eilmes 1, 2, 3, 4
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The first series of discrete multichromophore arrays of dibenzotetraaza[14]annulene (DBTAA), containing flexible bridges, have been synthesized in 40–46% isolated yields. The key asymmetrical intermediates, carrying two distinctly addressable functionalities (ROH vs. ROCH2–C![[triple bond, length as m-dash]](https://www.rsc.org/images/entities/char_e002.gif)
C–H and R(CH2)nBr vs. ROCH2–CC–H) at the macrocycle periphery, were synthesized in moderate to high (30–78%) isolated yields. Facile synthetic protocols developed for the synthesis of discrete DBTAA arrays offer several advantages such as operational simplicity and easy post-synthetic workup that overcome the need for laborious chromatographic purification. All new compounds were characterized by microanalysis, mass spectrometry, UV-Vis, FTIR-ATR, and 1H and 13C NMR spectroscopy. Structural features were briefly discussed with emphasis on several potential applications.
中文翻译：
二苯并四氮杂[14]环戊烯的多发色团阵列：生物有机化学的有前途的平台†
包含柔性桥的二苯并四氮杂[14]环戊二烯（DBTAA）的第一组离散多发色团阵列已合成，分离产率为40-46％。关键的不对称中间体，具有两个不同的可寻址功能（ROH与ROCH 2 –CC–H和R（CH 2）n Br与ROCH 2 –C大环外围的C–H）以中等到高（30–78％）的分离产率合成。为合成离散DBTAA阵列而开发的简便合成方案具有多个优点，例如操作简便和易于后合成后处理，从而无需进行费力的色谱纯化。所有新化合物均通过微量分析，质谱，UV-Vis，FTIR-ATR以及1 H和13 C NMR光谱进行了表征。简要讨论了结构特征，重点介绍了几种潜在的应用。
更新日期：2018-07-11
C–H and R(CH2)nBr vs. ROCH2–CC–H) at the macrocycle periphery, were synthesized in moderate to high (30–78%) isolated yields. Facile synthetic protocols developed for the synthesis of discrete DBTAA arrays offer several advantages such as operational simplicity and easy post-synthetic workup that overcome the need for laborious chromatographic purification. All new compounds were characterized by microanalysis, mass spectrometry, UV-Vis, FTIR-ATR, and 1H and 13C NMR spectroscopy. Structural features were briefly discussed with emphasis on several potential applications.
中文翻译：
二苯并四氮杂[14]环戊烯的多发色团阵列：生物有机化学的有前途的平台†
包含柔性桥的二苯并四氮杂[14]环戊二烯（DBTAA）的第一组离散多发色团阵列已合成，分离产率为40-46％。关键的不对称中间体，具有两个不同的可寻址功能（ROH与ROCH 2 –C
C–H和R（CH 2）n Br与ROCH 2 –C大环外围的C–H）以中等到高（30–78％）的分离产率合成。为合成离散DBTAA阵列而开发的简便合成方案具有多个优点，例如操作简便和易于后合成后处理，从而无需进行费力的色谱纯化。所有新化合物均通过微量分析，质谱，UV-Vis，FTIR-ATR以及1 H和13 C NMR光谱进行了表征。简要讨论了结构特征，重点介绍了几种潜在的应用。
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