{"doi":"10.1002/ejoc.201701609","title":"Unique Properties of 1,5‐Naphthyridin‐2(1<i>H</i>)‐one Derivatives as Environment‐Polarity‐Sensitive Fluorescent Dyes","abstract":"<jats:p>1,5‐Naphthyridin‐2(1<jats:italic>H</jats:italic>)‐one is structural component of the fluorescent natural products amarastelline A and nigakinone. Herein, we synthesized several 1,5‐naphthyridin‐2(1<jats:italic>H</jats:italic>)‐one derivatives and evaluated their fluorescence properties to examine their potential application as fluorescent probes. Among them, compounds that contain a 3‐hydroxyl group have unique solvent‐dependent fluorescence properties, that is, they exhibit stronger fluorescence in polar and protic solvents. The further installation of an 8‐phenyl group resulted in a shifted fluorescence in different solvents. Our results indicate that the 1,5‐naphthyridin‐2(1<jats:italic>H</jats:italic>)‐one scaffold would be a valuable and useful fluorophore that displays intense fluorescence relative to known bicyclic fluorophores such as hydroxyquinoline. Our findings suggest that the 1,5‐naphthyridin‐2(1<jats:italic>H</jats:italic>)‐one scaffold would be practical as an environment‐polarity‐dependent fluorophore, that is, for the development of sensors to detect structural changes in proteins and biomolecular interactions.</jats:p>","journal":"European Journal of Organic Chemistry","year":2018,"id":31619,"datarank":0.5873065035378872,"base_score":2.3978952727983707,"endowment":2.3978952727983707,"self_citation_contribution":0.3596842909197557,"citation_network_contribution":0.22762221261813145,"self_endowment_contribution":0.3596842909197557,"citer_contribution":0.22762221261813145,"corpus_percentile":null,"corpus_rank":null,"citation_count":10,"citer_count":8,"citers_with_citation_signal":8,"citers_with_endowment":8,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":null,"is_data_producer":false,"deposit_databanks":null,"is_oa":false,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":null,"fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":169068,"name":"Ayumi Ohsaki","orcid":"0000-0003-4895-7613","position":1,"is_corresponding":false},{"id":169070,"name":"Hiroyuki Kagechika","orcid":"0000-0002-6747-1013","position":2,"is_corresponding":false},{"id":169071,"name":"Tomoya Hirano","orcid":"0000-0003-1196-7199","position":3,"is_corresponding":false},{"id":169066,"name":"Hidetomo Yokoo","orcid":null,"position":0,"is_corresponding":false}],"reference_count":0,"raw_metadata":{"has_enrichment":true,"base_score":2.3978952727983707,"endowment":2.3978952727983707,"datacite_reuse_total":0,"file_count":0,"downloads":0,"views":0,"has_version_chain":false,"is_dataset":false,"is_oa":false,"pmid":"18998881","pmcid":null,"openalex_id":"https://openalex.org/W2772468872","authors":[],"funders":[],"total_grants":0,"fwci":0.1984,"citation_percentile":0.61368024,"influential_citations":0,"citation_trend":[{"year":2019,"count":1},{"year":2021,"count":1},{"year":2022,"count":1},{"year":2023,"count":4},{"year":2024,"count":3}],"oa_status":"closed","license":"http://onlinelibrary.wiley.com/termsAndConditions#vor","oa_locations":[{"url":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fejoc.201701609","host_type":"publisher"},{"url":"https://chemistry-europe.onlinelibrary.wiley.com/doi/pdf/10.1002/ejoc.201701609","host_type":"publisher"},{"url":"https://doi.org/10.1002/ejoc.201701609","host_type":"journal"}],"fields_of_study":["Synthesis of Organic Compounds","Oxidative Organic Chemistry Reactions","Synthesis of Indole Derivatives","Chemistry"],"mesh_terms":[],"keywords":["Fluorophore","Chemistry","Fluorescence","Solvent polarity","Polarity (international relations)","Solvent","Combinatorial chemistry","Photochemistry","Organic chemistry","Biochemistry"],"sdg_mappings":[],"linked_datasets":[],"clinical_trials":[],"software_tools":[],"database_accessions":[],"source":"live","citation_network_status":"fetched"},"created_at":"2026-06-09T07:48:27.284200Z","pmid":null,"pmcid":null,"fwci":null,"citation_percentile":null,"influential_citations":0,"oa_status":null,"license":null,"views":0,"total_file_size_bytes":0,"version_count":0,"fair_f":null,"fair_a":null,"fair_i":null,"fair_r":null,"fair_zscore":null,"fair_rationale":null,"fair_model":null,"fair_agent_version":null,"fair_fulltext_source":null,"fair_has_llm":null,"fair_computed_at":null,"clinical_trials":[],"software_tools":[],"db_accessions":[],"linked_datasets":[],"topics":[]}