Pub Date : 2025-11-14DOI: 10.1016/j.tet.2025.135060
Yuanfang Liu , Ruiying Pan , Xinni Xie , Jun Liu , Yuguo Du
A series of novel petrosiol E derivatives were synthesized by divergent strategies starting from readily available d-xylose as the chiral template. The pro-differentiating capacities of these derivatives were evaluated using a differentiation model of rat neuron-like PC12 cells and several derivatives exhibited moderate to significant pro-differentiating capacities. Our study demonstrated that the pro-differentiating capacities of these derivatives were very sensitive to modifications in the side chains, suggesting that the conjugated diyne skeleton and terminal alkyl residue might play important roles in the neuronal differentiation.
{"title":"Design, synthesis, and evaluation of petrosiol E derivatives on neuronal progenitors differentiation","authors":"Yuanfang Liu , Ruiying Pan , Xinni Xie , Jun Liu , Yuguo Du","doi":"10.1016/j.tet.2025.135060","DOIUrl":"10.1016/j.tet.2025.135060","url":null,"abstract":"<div><div>A series of novel petrosiol E derivatives were synthesized by divergent strategies starting from readily available <span>d</span>-xylose as the chiral template. The pro-differentiating capacities of these derivatives were evaluated using a differentiation model of rat neuron-like PC12 cells and several derivatives exhibited moderate to significant pro-differentiating capacities. Our study demonstrated that the pro-differentiating capacities of these derivatives were very sensitive to modifications in the side chains, suggesting that the conjugated diyne skeleton and terminal alkyl residue might play important roles in the neuronal differentiation.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"190 ","pages":"Article 135060"},"PeriodicalIF":2.2,"publicationDate":"2025-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145577159","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-11-14DOI: 10.1016/j.tet.2025.135064
Boris V. Lichitsky, Tatiana A. Kudryavtseva, Ekaterina N. Kudryavtseva
In the present communication we describe the construction of imidazo[4,5-b]indeno[2,1-e]pyridin-9(3H)-one system. The considered method is based on previously unknown multicomponent condensation of 5-aminoimidazoles with diverse aldehydes and 1,3-indandione. Sodium salts of 5-aminoimidazole-4-carboxylic acids were employed as convenient precursors for generation of unstable 5-aminoimidazoles in the reaction mixture. The application of easily available aromatic and heterocyclic aldehydes allowed us to obtain the array of target substituted imidazo[4,5-b]indeno[2,1-e]pyridin-9(3H)-ones. Atom economy, mild experimental conditions and simple isolation of the final products are the advantages of the method. X-ray analysis was utilized for confirmation of structure of one of the prepared imidazo[4,5-b]indeno[2,1-e]pyridin-9(3H)-ones.
{"title":"Straightforward synthesis of imidazo[4,5-b]indeno[2,1-e]pyridin-9(3H)-one framework via multicomponent reaction of 5-aminoimidazoles with aldehydes and 1,3-indandione","authors":"Boris V. Lichitsky, Tatiana A. Kudryavtseva, Ekaterina N. Kudryavtseva","doi":"10.1016/j.tet.2025.135064","DOIUrl":"10.1016/j.tet.2025.135064","url":null,"abstract":"<div><div>In the present communication we describe the construction of imidazo[4,5-<em>b</em>]indeno[2,1-<em>e</em>]pyridin-9(<em>3H)-</em>one system. The considered method is based on previously unknown multicomponent condensation of 5-aminoimidazoles with diverse aldehydes and 1,3-indandione. Sodium salts of 5-aminoimidazole-4-carboxylic acids were employed as convenient precursors for generation of unstable 5-aminoimidazoles in the reaction mixture. The application of easily available aromatic and heterocyclic aldehydes allowed us to obtain the array of target substituted imidazo[4,5-<em>b</em>]indeno[2,1-<em>e</em>]pyridin-9(<em>3H</em>)-ones. Atom economy, mild experimental conditions and simple isolation of the final products are the advantages of the method. X-ray analysis was utilized for confirmation of structure of one of the prepared imidazo[4,5-<em>b</em>]indeno[2,1-<em>e</em>]pyridin-9(<em>3H</em>)-ones.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"190 ","pages":"Article 135064"},"PeriodicalIF":2.2,"publicationDate":"2025-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145526718","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-11-13DOI: 10.1016/j.tet.2025.135063
João Pedro de Albuquerque Souza , Giuliana Pavaneli , Sandra Radžiutė , Caroline Da Ros Montes D'Oca , Vincas Būda , Paulo Henrique Gorgatti Zarbin
The chemical ecology of crane flies (Diptera: Tipulidae) has only recently begun to be elucidated, creating a pressing need for enantiomerically pure standards to support structural identification and functional studies. In a previous investigation, the cuticular hydrocarbons (R)- and (S)-3-methylheneicosane were identified as male-specific components of Tipula autumnalis, with synthetic samples enabling both confirmation of their stereostructures and assessment of biological activity. Laboratory bioassays revealed that the (R)-enantiomer elicited an excitatory response in males, whereas the (S)-enantiomer acted as a repellent. In the present work, we detail the total enantiospecific synthesis of these compounds from methyl (S)-3-hydroxy-2-methylpropionate precursor. The route employs orthogonal protection, Wittig coupling with a C17 fragment, hydrogenation, and terminal one-carbon homologation, providing efficient access to long-chain methyl-branched hydrocarbons with full stereochemical control. This work establishes a robust and generalizable strategy for the synthesis of enantioenriched methyl-branched hydrocarbons and provides sufficient material to support all future chemical and behavioral studies in this species, paving the way for the development of targeted insect management strategies.
{"title":"Enantiospecific syntheses of (R)- and (S)-3-methylheneicosane, male-specific cuticular hydrocarbon of the crane fly Tipula autumnalis (Diptera: Tipulidae)","authors":"João Pedro de Albuquerque Souza , Giuliana Pavaneli , Sandra Radžiutė , Caroline Da Ros Montes D'Oca , Vincas Būda , Paulo Henrique Gorgatti Zarbin","doi":"10.1016/j.tet.2025.135063","DOIUrl":"10.1016/j.tet.2025.135063","url":null,"abstract":"<div><div>The chemical ecology of crane flies (Diptera: Tipulidae) has only recently begun to be elucidated, creating a pressing need for enantiomerically pure standards to support structural identification and functional studies. In a previous investigation, the cuticular hydrocarbons (<em>R</em>)- and (<em>S</em>)-3-methylheneicosane were identified as male-specific components of <em>Tipula autumnalis</em>, with synthetic samples enabling both confirmation of their stereostructures and assessment of biological activity. Laboratory bioassays revealed that the (<em>R</em>)-enantiomer elicited an excitatory response in males, whereas the (<em>S</em>)-enantiomer acted as a repellent. In the present work, we detail the total enantiospecific synthesis of these compounds from methyl (<em>S</em>)-3-hydroxy-2-methylpropionate precursor. The route employs orthogonal protection, Wittig coupling with a C17 fragment, hydrogenation, and terminal one-carbon homologation, providing efficient access to long-chain methyl-branched hydrocarbons with full stereochemical control. This work establishes a robust and generalizable strategy for the synthesis of enantioenriched methyl-branched hydrocarbons and provides sufficient material to support all future chemical and behavioral studies in this species, paving the way for the development of targeted insect management strategies.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"190 ","pages":"Article 135063"},"PeriodicalIF":2.2,"publicationDate":"2025-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145527168","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-11-12DOI: 10.1016/j.tet.2025.135057
Jiahong Chen, Yuanyuan Huang, Nan Wang, You Zi
A practical and N-selective allylation of sulfenamides using Morita-Baylis-Hillman carbonates under Lewis base catalysis is reported. It features broad substrate scope, high chemoselectivity, and tolerance to various functional groups, affording diverse N-allylated sulfenamides in good to excellent yields. Gram-scale experiments confirm its scalability, facilitating the synthesis of bioactive molecules and expanding the utility of sulfenamide chemistry.
{"title":"Lewis base catalyzed N-selective allylation of sufenamides with Morita–Baylis–Hillman carbonates","authors":"Jiahong Chen, Yuanyuan Huang, Nan Wang, You Zi","doi":"10.1016/j.tet.2025.135057","DOIUrl":"10.1016/j.tet.2025.135057","url":null,"abstract":"<div><div>A practical and N-selective allylation of sulfenamides using Morita-Baylis-Hillman carbonates under Lewis base catalysis is reported. It features broad substrate scope, high chemoselectivity, and tolerance to various functional groups, affording diverse N-allylated sulfenamides in good to excellent yields. Gram-scale experiments confirm its scalability, facilitating the synthesis of bioactive molecules and expanding the utility of sulfenamide chemistry.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"190 ","pages":"Article 135057"},"PeriodicalIF":2.2,"publicationDate":"2025-11-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145526717","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Indoles are critical heterocycles present in various biologically active compounds, such as medicines. Therefore, the introduction of a fluoro substituent into an indole nucleus is of great interest from the viewpoints of both synthetic and medicinal chemistry. This study successfully synthesized 2-trifluoromethylindole-3-acetic acid derivatives by reacting o-trifluoroacetamidocinnamic acid derivatives with tributylphosphine under thermolytic decomposition conditions. Although the 1-unsubstituted 2-trifluoromethylindoles were obtained without using an additional additive, the 1-alkyl substituted ones required benzoic acid as an additive. An analog of indomethacin with a trifluoromethyl group in place of the methyl group was synthesized using this method.
{"title":"Synthesis of 2-trifluoromethylindole-3-acetic acid derivatives from o-trifluoroacetamidocinnamic acid derivatives by 1,4-addition of tributylphosphine and thermolysis","authors":"Yoshiko Chihara, Manami Itoh, Shiho Takahashi, Yuka Yamasaki, Haruka Kasaya, Masahiro Ikejiri, Kazuyuki Miyashita, Aki Fujisaka","doi":"10.1016/j.tet.2025.135062","DOIUrl":"10.1016/j.tet.2025.135062","url":null,"abstract":"<div><div>Indoles are critical heterocycles present in various biologically active compounds, such as medicines. Therefore, the introduction of a fluoro substituent into an indole nucleus is of great interest from the viewpoints of both synthetic and medicinal chemistry. This study successfully synthesized 2-trifluoromethylindole-3-acetic acid derivatives by reacting <em>o</em>-trifluoroacetamidocinnamic acid derivatives with tributylphosphine under thermolytic decomposition conditions. Although the 1-unsubstituted 2-trifluoromethylindoles were obtained without using an additional additive, the 1-alkyl substituted ones required benzoic acid as an additive. An analog of indomethacin with a trifluoromethyl group in place of the methyl group was synthesized using this method.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"190 ","pages":"Article 135062"},"PeriodicalIF":2.2,"publicationDate":"2025-11-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145527169","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-11-11DOI: 10.1016/j.tet.2025.135058
Matthew A. Horwitz , Jose Manuel Villalgordo , Maria Gonzalez Perez , Nektarios Kranidiotis-Hisatomi , Anna Mrowiec , Martin Walker , Vanessa Jahnke , Laure Breuils , Justine Chaigne , Axel Reix , Romain Boutillier , Xavier Fontenault , Carleton Sage
A late-stage diversification strategy for the synthesis of novel BCR/ABL tyrosine kinase inhibitors is reported. A uniquely selective bromination reagent was applied to the functionalization of nilotinib, radotinib, and imatinib at a single site, enabling the facile generation of new derivatives of these scaffolds. The novel derivatives were profiled through enzymatic activity assays, cellular target engagement assays, and ADME assays. By exploring inhibition profiles across a range of ABL mutants, it was found that nilotinib derivatives 20 and 21 exhibit broad inhibitory activity, which is superior to the parent compound for some ABL isoforms.
{"title":"Leveraging selective late-stage functionalization reactions for SAR vector interrogation in BCR/ABL kinase inhibitors","authors":"Matthew A. Horwitz , Jose Manuel Villalgordo , Maria Gonzalez Perez , Nektarios Kranidiotis-Hisatomi , Anna Mrowiec , Martin Walker , Vanessa Jahnke , Laure Breuils , Justine Chaigne , Axel Reix , Romain Boutillier , Xavier Fontenault , Carleton Sage","doi":"10.1016/j.tet.2025.135058","DOIUrl":"10.1016/j.tet.2025.135058","url":null,"abstract":"<div><div>A late-stage diversification strategy for the synthesis of novel BCR/ABL tyrosine kinase inhibitors is reported. A uniquely selective bromination reagent was applied to the functionalization of nilotinib, radotinib, and imatinib at a single site, enabling the facile generation of new derivatives of these scaffolds. The novel derivatives were profiled through enzymatic activity assays, cellular target engagement assays, and ADME assays. By exploring inhibition profiles across a range of ABL mutants, it was found that nilotinib derivatives <strong>20</strong> and <strong>21</strong> exhibit broad inhibitory activity, which is superior to the parent compound for some ABL isoforms.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"190 ","pages":"Article 135058"},"PeriodicalIF":2.2,"publicationDate":"2025-11-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145526715","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
An iron-catalyzed [4 + 2] cyclization for constructing 4-Arylpyrimido[1,2-b] indazoles using 3-Aminopyrazole, phenylacetylene and N, N-Dimethylformamide has been reported, where N, N-Dimethylformamide (DMF) acted one-carbon synthon. The reaction conditions are mild and rapid, with a wide range of applicable substrates.
{"title":"Iron-catalyzed synthesis of 4-arylpyrimido[1,2-b]indazoles using 3-aminobenzindazole, phenylacetylene, and N,N-dimethylformamide as one-carbon synthon","authors":"Yifan Song , Suqin Shang , Qian Guo, Xiaoqing Deng, Xinxin Jia, Mengyi Guo, Luoteng Cheng, Jianyong Yuan","doi":"10.1016/j.tet.2025.135059","DOIUrl":"10.1016/j.tet.2025.135059","url":null,"abstract":"<div><div>An iron-catalyzed [4 + 2] cyclization for constructing 4-Arylpyrimido[1,2-b] indazoles using 3-Aminopyrazole, phenylacetylene and <em>N, N</em>-Dimethylformamide has been reported, where <em>N, N</em>-Dimethylformamide (DMF) acted one-carbon synthon. The reaction conditions are mild and rapid, with a wide range of applicable substrates.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"190 ","pages":"Article 135059"},"PeriodicalIF":2.2,"publicationDate":"2025-11-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145526716","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-11-07DOI: 10.1016/j.tet.2025.135044
Shikai Yang , Ziyan Wu , Xindi Li , Jinshan Li , Hongtao Liu , Juanzu Liu , Chunman Jia
A simple and practical synthetic route for the scalable synthesis of highly valuable α-trifluoromethylated indole-3-carbinols with more cost-effective trifluoroacetaldehyde hydrate has been developed. This convenient recyclable H-bonding HFIP-promoted synthetic protocol allows the rapid construction of structurally diverse α-trifluoromethylated indole-3-carbinols with high efficiency. The synthetic utility of this protocol is further highlighted by the decagram-scale synthesis and product derivatizations.
{"title":"A practical and scalable synthetic protocol for α-trifluoromethylated indole-3-carbinols","authors":"Shikai Yang , Ziyan Wu , Xindi Li , Jinshan Li , Hongtao Liu , Juanzu Liu , Chunman Jia","doi":"10.1016/j.tet.2025.135044","DOIUrl":"10.1016/j.tet.2025.135044","url":null,"abstract":"<div><div>A simple and practical synthetic route for the scalable synthesis of highly valuable α-trifluoromethylated indole-3-carbinols with more cost-effective trifluoroacetaldehyde hydrate has been developed. This convenient recyclable H-bonding HFIP-promoted synthetic protocol allows the rapid construction of structurally diverse α-trifluoromethylated indole-3-carbinols with high efficiency. The synthetic utility of this protocol is further highlighted by the decagram-scale synthesis and product derivatizations.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"190 ","pages":"Article 135044"},"PeriodicalIF":2.2,"publicationDate":"2025-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145475102","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-11-07DOI: 10.1016/j.tet.2025.135045
Alan C. Cecil, Evans Fosu, Bruno Donnadieu, T. Keith Hollis
Copper-mediated methodologies for the arylation of bis-azolium salts and bis-azoles are efficient pathways to access symmetrical and unsymmetrical N-heterocyclic carbene precursors. The arylation of bis-azolium salts with various aryl halides was achieved in moderate yields to furnish numerous C2-arylated bis-azolium salts. Access of C2-arylated bis-azolium salts from bis-azoles was also achieved in a single pot domino reaction via the use of iodonium salts as embedded electrophiles. The latter methodology utilizes the aryl iodide byproduct from the N-arylation step for the C–H activation step to mitigate waste and the need to recycle. We also demonstrated the use of these azolium salts in metalation and found success in obtaining metal complexes containing abnormal N-heterocyclic carbenes.
{"title":"Bis-arylation of phenylene-bridged bis-azolium salts and tetra-arylation of bis-azoles to access symmetrical and unsymmetrical CCC-aNHC pincer ligand precursors","authors":"Alan C. Cecil, Evans Fosu, Bruno Donnadieu, T. Keith Hollis","doi":"10.1016/j.tet.2025.135045","DOIUrl":"10.1016/j.tet.2025.135045","url":null,"abstract":"<div><div>Copper-mediated methodologies for the arylation of bis-azolium salts and bis-azoles are efficient pathways to access symmetrical and unsymmetrical <em>N</em>-heterocyclic carbene precursors. The arylation of bis-azolium salts with various aryl halides was achieved in moderate yields to furnish numerous C2-arylated bis-azolium salts. Access of C2-arylated bis-azolium salts from bis-azoles was also achieved in a single pot domino reaction via the use of iodonium salts as embedded electrophiles. The latter methodology utilizes the aryl iodide byproduct from the N-arylation step for the C–H activation step to mitigate waste and the need to recycle. We also demonstrated the use of these azolium salts in metalation and found success in obtaining metal complexes containing abnormal <em>N</em>-heterocyclic carbenes.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"190 ","pages":"Article 135045"},"PeriodicalIF":2.2,"publicationDate":"2025-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145526712","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-11-06DOI: 10.1016/j.tet.2025.135042
Shaoling Li , Xiaoxue Chen , Jialin Li , Tao Jiang , Wei Liu , Kai Yan , Junru Chen , Md Monarul Islam , Carl Redshaw , Xing Feng
Organic light-emitting diodes (OLEDs) are significantly affected by the photophysical features of organic luminescent materials. In this article, a series of pyrene-based luminogens 2 and 3 are synthesized from a bromopyrene precursor, namely 1,3,6,8-tetrabromopyrene-2,7-diol 1, by a Suzuki-Miyaura coupling reaction and subsequent substitution reaction, where the bromo and hydroxyl groups at the pyrene core can be readily modified to obtain the target products. The developed fluorophores exhibit a strong blue emission with a narrow full width at half maximum, as well as excellent solid-state emission efficiency by regulating molecular flexibility.
{"title":"The effect of molecular flexibility on the optical properties of triphenylamine/benzocarbazole-decorated tetrakis-substituted pyrene-based blue emitters","authors":"Shaoling Li , Xiaoxue Chen , Jialin Li , Tao Jiang , Wei Liu , Kai Yan , Junru Chen , Md Monarul Islam , Carl Redshaw , Xing Feng","doi":"10.1016/j.tet.2025.135042","DOIUrl":"10.1016/j.tet.2025.135042","url":null,"abstract":"<div><div>Organic light-emitting diodes (OLEDs) are significantly affected by the photophysical features of organic luminescent materials. In this article, a series of pyrene-based luminogens <strong>2</strong> and <strong>3</strong> are synthesized from a bromopyrene precursor, namely 1,3,6,8-tetrabromopyrene-2,7-diol <strong>1,</strong> by a Suzuki-Miyaura coupling reaction and subsequent substitution reaction, where the bromo and hydroxyl groups at the pyrene core can be readily modified to obtain the target products. The developed fluorophores exhibit a strong blue emission with a narrow full width at half maximum, as well as excellent solid-state emission efficiency by regulating molecular flexibility.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"190 ","pages":"Article 135042"},"PeriodicalIF":2.2,"publicationDate":"2025-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145526714","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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