Increasing Scope of Clickable Fluorophores: Electrophilic Substitution of Ylidenemalononitriles

Autor(es)

de Souza, Juliana M. ^{[1, 2]} ; Abdiaj, Irini ^[2] ; Chen, Jiaqi ^[3] ; Hanson, Kenneth ^[3] ; de Oliveira, Kleber T. ^[1] ; McQuade, D. Tyler ^[2]

Afiliação do(s) autor(es)

^[1] Univ Fed Sao Carlos, Dept Quim, BR-13565905 Sao Carlos, SP - Brazil

^[2] Virginia Commonwealth Univ, Dept Chem & Life Sci Engn, Richmond, VA 23284 - USA

^[3] Florida State Univ, Dept Chem & Biochem, Tallahassee, FL 32306 - USA

• Tipo de documento: Artigo Científico
• Fonte: Journal of Organic Chemistry; v. 85, n. 18, p. 11822-11834, SEP 18 2020.
• Citações Web of Science: 1

Resumo

Recently, we demonstrated that ylidenemalononitriles (YMs) react with amines to form cyclic amidines and that the starting linear YMs are nonemissive in solution and the cyclic amidines are fluorescent. These turn-on systems were of interest to us because of their potential as biosensors and synthons for accessing functionalized pyridines. While our original method was promising, several limitations persisted, including access to more functionalized and polar-solvent-soluble structures as well as increased control over the rate of cyclization. Herein, we report a new approach that allows the electrophilic substitution of YMs. These substituted YMs exhibit faster turn-on rates, color tunability, access to polar-solvent-soluble species, and increased control over cyclization rate. This allowed us to significantly expand the fluorophore's chemical space. (AU)

• Processo FAPESP: 18/14555-8 - Reações químicas em regime de fluxo contínuo: aspectos químicos e econômicos da utilização de tecnologias facilitadoras na obtenção de medicamentos de baixo custo
• Beneficiário: Kleber Thiago de Oliveira
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• Processo FAPESP: 18/00106-7 - Reações Fotocatalisadas por Porfirinas em Condições de Fluxo Contínuo: Arilação de Sistemas Heterocíclicos e de Olefinas Ativadas
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