{"doi":"10.1002/asia.202300489","title":"Design and Synthesis of Far‐Red to Near‐Infrared Chromophores with Pyrazine‐Based Boron Complexes","abstract":"<jats:title>Abstract</jats:title><jats:p>We synthesized new binuclear boron complexes based on pyrazine with <jats:italic>ortho</jats:italic> and <jats:italic>para</jats:italic> substitution patterns. It was demonstrated that the <jats:italic>para</jats:italic>‐linked complexes possess a significantly narrow energy gap between highest occupied and lowest unoccupied molecular orbitals (HOMO and LUMO), leading to their far‐red to near‐infrared emission properties. Meanwhile, the ortho‐substituted complex showed orange emission. Considering the HOMO and LUMO distributions of pyrazine, the boron complexation to the nitrogen atoms would stabilize its LUMO more efficiently than its HOMO because a nodal plane in the HOMO passes through the two nitrogen atoms. The theoretical study suggests that the <jats:italic>para</jats:italic>‐substitution would not significantly perturb such a characteristic HOMO distribution originating from pyrazine in stark contrast to the <jats:italic>ortho</jats:italic>‐substituted one. As a result, the HOMO‐LUMO gap of the <jats:italic>para</jats:italic>‐linked complex is dramatically narrower than that of the <jats:italic>ortho</jats:italic>‐linked one.</jats:p>","journal":"Chemistry – An Asian Journal","year":2023,"id":42556,"datarank":0.4044962472735143,"base_score":2.1972245773362196,"endowment":2.1972245773362196,"self_citation_contribution":0.32958368660043297,"citation_network_contribution":0.07491256067308133,"self_endowment_contribution":0.32958368660043297,"citer_contribution":0.07491256067308133,"corpus_percentile":null,"corpus_rank":null,"citation_count":8,"citer_count":5,"citers_with_citation_signal":4,"citers_with_endowment":4,"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":152562,"name":"Hiroyuki Watanabe","orcid":null,"position":1,"is_corresponding":false},{"id":203550,"name":"Shunichiro Ito","orcid":"0000-0003-3822-0247","position":2,"is_corresponding":false},{"id":203551,"name":"Kazuo Tanaka","orcid":"0000-0001-6571-7086","position":3,"is_corresponding":false},{"id":203552,"name":"Yoshiki Chujo","orcid":null,"position":4,"is_corresponding":false},{"id":203549,"name":"Hiromasa Takahashi","orcid":null,"position":0,"is_corresponding":false}],"reference_count":0,"raw_metadata":{"has_enrichment":true,"base_score":2.1972245773362196,"endowment":2.1972245773362196,"datacite_reuse_total":0,"file_count":0,"downloads":0,"views":0,"has_version_chain":false,"is_dataset":false,"is_oa":false,"pmid":"37365136","pmcid":null,"openalex_id":"https://openalex.org/W4382049677","authors":[],"funders":[{"funder_name":"JSPS KAKENHI","grant_id":"21K19002","title":null},{"funder_name":"The Ministry of Education, Culture, Sports, Science, and Technology, Japan","grant_id":"JP24102013","title":null},{"funder_name":"The Ministry of Education, Culture, Sports, Science, and Technology, Japan","grant_id":"2401","title":null},{"funder_name":"JSPS KAKENHI","grant_id":"21H02001","title":null},{"funder_name":"JSPS KAKENHI","grant_id":"21K14673","title":null},{"funder_name":"JSPS KAKENHI","grant_id":"23K13793","title":null},{"funder_name":"Kato Foundation for Promotion of Science","grant_id":"","title":null},{"funder_name":"Grant-in-Aid for Early-Career Scientists","grant_id":"","title":null},{"funder_name":"Kato Foundation for Promotion of Science","grant_id":"","title":null},{"funder_name":"Grant-in-Aid for Early-Career Scientists","grant_id":"","title":null}],"total_grants":10,"fwci":0.7261,"citation_percentile":0.64114249,"influential_citations":0,"citation_trend":[{"year":2023,"count":2},{"year":2024,"count":3},{"year":2025,"count":3}],"oa_status":"green","license":"http://onlinelibrary.wiley.com/termsAndConditions#vor","oa_locations":[{"url":"http://hdl.handle.net/2433/284855","host_type":"repository"},{"url":"https://repository.kulib.kyoto-u.ac.jp/dspace/bitstream/2433/284855/1/asia.202300489.pdf","host_type":"GREEN"},{"url":"http://hdl.handle.net/2433/284855","host_type":"repository"},{"url":"https://aces.onlinelibrary.wiley.com/doi/pdf/10.1002/asia.202300489","host_type":"publisher"},{"url":"https://doi.org/10.1002/asia.202300489","host_type":"journal"},{"url":"https://pubmed.ncbi.nlm.nih.gov/37365136","host_type":"repository"}],"fields_of_study":["Luminescence and Fluorescent Materials","Organic Light-Emitting Diodes Research","Synthesis and Properties of Aromatic Compounds","Medicine","Chemistry"],"mesh_terms":[],"keywords":["Pyrazine","HOMO/LUMO","Boron","Chromophore","Photochemistry","Chemistry","Infrared","Crystallography","Nitrogen","Atomic orbital","Molecular orbital","Stereochemistry","Molecule","Physics","Organic chemistry","Optics","Fluorescence","Near-infrared Emission","Aggregation-induced Emission Enhancement"],"sdg_mappings":[{"sdg_number":0,"sdg_label":"Affordable and clean energy"}],"linked_datasets":[],"clinical_trials":[],"software_tools":[],"database_accessions":[],"source":"live","citation_network_status":"fetched"},"created_at":"2026-06-14T03:41:59.128797Z","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":[]}