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Structure–Photochemical Function Relationships in Nitrogen-Containing Heterocyclic Aromatic Photobases Derived from Quinoline
The Journal of Physical Chemistry A ( IF 2.9 ) Pub Date : 2020-03-20 , DOI: 10.1021/acs.jpca.9b11375
Sophya F. Alamudun 1 , Kyle Tanovitz 1 , April Fajardo 1 , Kaitlind Johnson 1 , Andy Pham 1 , Tina Jamshidi Araghi 1 , Andrew S. Petit 1
Affiliation  

Photobases are compounds that become strong bases after electronic excitation. Recent experimental studies have highlighted the photobasicity of the 5-R quinoline compounds, demonstrating a strong substituent dependence to the pKa*. In this paper, we describe our systematic study of how the thermodynamic driving force for photobasicity is tuned through substituents in four families of nitrogen-containing heterocyclic aromatics. We show that substituent position and identity both significantly impact the pKa*. We demonstrate that the substituent effects are additive and identify many disubstituted compounds with substantially greater photobasicity than the most photobasic 5-R quinoline compound identified previously. We show that the addition of a second fused benzene ring to quinoline, along with two electron-donating substituents, lowers the S0 → SPBS vertical excitation energy into the visible region while still maintaining a pKa* > 14. Overall, the structure–function relationships developed in this study provide new insights to guide the development of new photocatalysts that employ photobasicity.

中文翻译:

喹啉衍生的含氮杂环芳族光碱中的结构-光化学功能关系

光碱是在电子激发后变成强碱的化合物。最近的实验研究突出了5-R喹啉化合物的光碱性,表明对p K a *的强烈取代基依赖性。在本文中,我们描述了如何通过四个含氮杂环芳族化合物中的取代基调节光碱性的热力学驱动力的系统研究。我们表明,取代基的位置和同一性均会显着影响p K a *。我们证明取代基的作用是加和的,并鉴定出许多比以前鉴定的最光碱性的5-R喹啉化合物具有更大的光碱性的二取代化合物。我们表明,向喹啉中添加第二个稠合苯环以及两个供电子取代基可将S 0 →S PBS垂直激发能降低到可见光区域,同时仍保持ap K a * >14。总体而言,结构–本研究中开发的功能关系提供了新见解,可指导开发采用光碱性的新型光催化剂。
更新日期:2020-03-21
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