Methyl‐ and Methoxy‐substituted 2‐(Pyridin‐2‐yl)‐4‐(4‐aminophenyl)quinazolines: Synthesis and Photophysical Properties

IF 2.8 4区 化学 Q1 CHEMISTRY, ORGANIC Asian Journal of Organic Chemistry Pub Date : 2024-07-01 DOI:10.1002/ajoc.202400135
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Abstract

A series of novel 2‐(2‐pyridyl)quinazoline luminophores containing a donor aryl fragment at position 4 and methyl or methoxy groups at benzene ring has been synthesized by efficient three‐step route. The linear optical properties have been studied by UV/Vis absorption and photoluminescence spectra in two solvents. We revealed that introduction of additional methyl group or the replacement of methyl substituents with methoxy ones lead to sequentially shift of absorption and emission maximum to blue region. 9H‐Carbazol‐9‐yl‐containing derivative is characterized by hypsochromically shifted absorption band compared to its NEt2 and NPh2 counterparts. Unlike 9H‐carbazol‐9‐yl‐derivative, Et2N‐ and Ph2N‐bearing quinazolines demonstrate considerable decrease in quantum yield values when going from toluene to MeCN. Solvatochromic properties have been explored, the pronounced bathochromic shift was observed in fluorescence spectra with the increase of solvents polarity. Moreover, the compounds show significant shift of emission band with the increase of water fraction in DMSO/H2O mixture. Two‐photon optical properties have been also studied, the two‐photon absorption cross‐sections in MeCN and toluene reached 120 GM and 210 GM, respectively. The presence of additional methyl group has little impact on δTPA value, while introduction of methoxy substituents dramatically decreases TPA cross sections. Additionally, a quantumchemical calculations of synthesized compounds were performed to support the experimental data.

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甲基和甲氧基取代的 2-(吡啶-2-基)-4-(4-氨基苯基)喹唑啉:合成与光物理性质
通过高效的三步法合成了一系列 2-(2-吡啶基)喹唑啉发光体,其第 4 位含有供体芳基片段,苯环上含有甲基或甲氧基。在两种溶剂中通过紫外/可见吸收光谱和光致发光光谱对其线性光学特性进行了研究。我们发现,引入额外的甲基或用甲氧基取代甲基取代基会导致吸收和发射最大值依次转移到蓝色区域。与 NEt2 和 NPh2 对应衍生物相比,含 9H-咔唑-9-基的衍生物的吸收带具有低色移的特点。与 9H-咔唑-9-基衍生物不同,当从甲苯转移到 MeCN 时,Et2N- 和 Ph2N-喹唑啉的量子产率值会有相当大的下降。对溶解变色特性进行了研究,发现随着溶剂极性的增加,荧光光谱会发生明显的溶解变色偏移。此外,随着 DMSO/H2O 混合物中水含量的增加,化合物的发射带也发生了明显的移动。还研究了双光子光学特性,在 MeCN 和甲苯中的双光子吸收截面分别达到 120 GM 和 210 GM。额外甲基的存在对δTPA 的影响很小,而甲氧基取代基的引入会显著降低 TPA 的截面。此外,还对合成的化合物进行了量子化学计算,以支持实验数据。
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来源期刊
CiteScore
4.70
自引率
3.70%
发文量
372
期刊介绍: Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.
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