{"doi":"10.1002/hlca.201800153","title":"Functionalization at C(1) of the Dihydroazulene/Vinylheptafulvene Photo‐/Thermoswitch – Establishing Structure−Property Relationship","abstract":"<jats:title>Abstract</jats:title><jats:p>The optical and switching properties of the dihydroazulene/vinylheptafulvene (DHA/VHF) photo‐/thermoswitch can be finely tuned by substituent groups at specific positions. While the kinetics of the thermal ring closure of VHF into DHA have previously been shown to follow systematic trends in regard to the electron‐withdrawing/donating character of substituents at DHA positions C(2), C(3), and C(7) (<jats:italic>Hammett</jats:italic> correlations), no such correlation has so far been established for a selection of compounds with different substituents at C(1). Functionalization at this position is at the same time known to have the strongest impact on the VHF‐to‐DHA conversion rate. Here we show that introduction of a benzothiazole ring at C(1) of DHA (corresponding to the vinyl position of VHF) with various electron‐withdrawing/donating groups provides VHFs whose rates of ring closure follow a <jats:italic>Hammett</jats:italic> correlation – the more electron‐withdrawing substituent on the benzothiazole, the faster ring closure reaction.</jats:p>","journal":"Helvetica Chimica Acta","year":2018,"id":42562,"datarank":0.29983054465476283,"base_score":1.791759469228055,"endowment":1.791759469228055,"self_citation_contribution":0.26876392038420827,"citation_network_contribution":0.031066624270554583,"self_endowment_contribution":0.26876392038420827,"citer_contribution":0.031066624270554583,"corpus_percentile":null,"corpus_rank":null,"citation_count":5,"citer_count":1,"citers_with_citation_signal":1,"citers_with_endowment":1,"datacite_reuse_total":1,"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":203571,"name":"Martin Drøhse Kilde","orcid":null,"position":1,"is_corresponding":false},{"id":203572,"name":"Anders Kadziola","orcid":null,"position":2,"is_corresponding":false},{"id":203573,"name":"Martina Cacciarini","orcid":null,"position":3,"is_corresponding":false},{"id":203574,"name":"Mogens Brøndsted Nielsen","orcid":null,"position":4,"is_corresponding":false},{"id":203570,"name":"Dianna Andersen","orcid":null,"position":0,"is_corresponding":false}],"reference_count":0,"raw_metadata":{"has_enrichment":true,"base_score":1.791759469228055,"endowment":1.791759469228055,"datacite_reuse_total":1,"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/W2889813305","authors":[],"funders":[],"total_grants":0,"fwci":0.2969,"citation_percentile":0.51936444,"influential_citations":0,"citation_trend":[{"year":2019,"count":2},{"year":2020,"count":1},{"year":2022,"count":1},{"year":2025,"count":1}],"oa_status":"closed","license":"http://onlinelibrary.wiley.com/termsAndConditions#vor","oa_locations":[{"url":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fhlca.201800153","host_type":"publisher"},{"url":"https://onlinelibrary.wiley.com/doi/pdf/10.1002/hlca.201800153","host_type":"publisher"},{"url":"https://doi.org/10.1002/hlca.201800153","host_type":"journal"},{"url":"http://hdl.handle.net/2158/1134942","host_type":"repository"}],"fields_of_study":["Photochromic and Fluorescence Chemistry","Photoreceptor and optogenetics research","Organic Chemistry Cycloaddition Reactions","Chemistry","Materials Science"],"mesh_terms":[],"keywords":["Substituent","Benzothiazole","Chemistry","Ring (chemistry)","Polar effect","Surface modification","Closure (psychology)","Stereochemistry","Medicinal chemistry","Organic chemistry","Physical chemistry"],"sdg_mappings":[{"sdg_number":0,"sdg_label":"Clean water and sanitation"}],"linked_datasets":[{"doi":"10.5517/ccdc.csd.cc209xmw","title":"CCDC 1856578: Experimental Crystal Structure Determination","publisher":"Cambridge Crystallographic Data Centre","resource_type":"Dataset"}],"clinical_trials":[],"software_tools":[],"database_accessions":[],"source":"live","citation_network_status":"fetched"},"created_at":"2026-06-14T03:42:50.444851Z","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":[]}