{"title":"Methyl‐ and Methoxy‐substituted 2‐(Pyridin‐2‐yl)‐4‐(4‐aminophenyl)quinazolines: Synthesis and Photophysical Properties","authors":"","doi":"10.1002/ajoc.202400135","DOIUrl":null,"url":null,"abstract":"<div><p>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<em>/</em>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. 9<em>H</em>‐Carbazol‐9‐yl‐containing derivative is characterized by hypsochromically shifted absorption band compared to its NEt<sub>2</sub> and NPh<sub>2</sub> counterparts. Unlike 9<em>H</em>‐carbazol‐9‐yl‐derivative, Et<sub>2</sub>N‐ and Ph<sub>2</sub>N‐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/H<sub>2</sub>O 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 δ<sub>TPA</sub> value, while introduction of methoxy substituents dramatically decreases TPA cross sections. Additionally, a quantum<em>‐</em>chemical calculations of synthesized compounds were performed to support the experimental data.</p></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.8000,"publicationDate":"2024-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Asian Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S2193580724001065","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
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 quantum‐chemical calculations of synthesized compounds were performed to support the experimental data.
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.