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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Increasing Scope of Clickable Fluorophores: Electrophilic Substitution of Ylidenemalononitriles

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Author(s):
de Souza, Juliana M. [1, 2] ; Abdiaj, Irini [2] ; Chen, Jiaqi [3] ; Hanson, Kenneth [3] ; de Oliveira, Kleber T. [1] ; McQuade, D. Tyler [2]
Total Authors: 6
Affiliation:
[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
Total Affiliations: 3
Document type: Journal article
Source: Journal of Organic Chemistry; v. 85, n. 18, p. 11822-11834, SEP 18 2020.
Web of Science Citations: 1
Abstract

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)

FAPESP's process: 18/14555-8 - Chemical reactions under continuous flow conditions: chemical and economic aspects of the use of enabling technologies for obtaining low cost medicines
Grantee:Kleber Thiago de Oliveira
Support Opportunities: Research Grants - Visiting Researcher Grant - International
FAPESP's process: 18/00106-7 - Photocatalyzed Reactions by using porphyrins and continuous flow conditions: Arylations of heterocycles and activated olefins.
Grantee:Kleber Thiago de Oliveira
Support Opportunities: Regular Research Grants