Fluorescence from bisaryl-substituted maleimide derivatives

Author(s)

Lauer, Milena Helmer ^[1] ; Drekener, Roberta Lopes ^[2] ; Duarte Correia, Carlos Roque ^[2] ; Gehlen, Marcelo Henrique ^[1]

Affiliation

^[1] Univ Sao Paulo, Inst Chem Sao Carlos, BR-13560590 Sao Carlos, SP - Brazil

^[2] Univ Estadual Campinas, Inst Chem, BR-13083862 Campinas, SP - Brazil

• Document type: Journal article
• Source: PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES; v. 13, n. 6, p. 859-866, 2014.
• Web of Science Citations: 11

Abstract

A series of bisaryl-substituted fluorescent maleimides was synthesized via the Heck arylation. The compounds showed broad fluorescence emission bands in the visible region, a large Stokes shift in polar solvents and emission quantum yields varying from 0.04 to 0.71, depending on the structure and solvent medium. The difference in dipole moments of ground and excited electronic states of about 12 Debye is ascribed to a substantial charge shift and push-pull character of bisaryl-substituted maleimides. The fluorescence decays of N-benzyl-3,4-bis(4-methoxyphenyl)-1H-pyrrole-2,5-dione (compound 5a) are biexponential with short (1.3-7.6 ns) and long lived (11.5-13.6 ns) components in polar solvents, but in 1,4-dioxane and THF the decays become single exponential. On the other hand, N-benzyl-3-(4-methoxyphenyl)-4-(4-hydroxyphenyl)-1H-pyrrole-2,5-dione (compound 5b) exhibited a biexponential decay in DMSO and in DMF with much shorter decay components, and such behavior indicated a charge shift process combined with solvent assisted proton transfer in the excited state. (AU)

• FAPESP's process: 11/18215-8 - Advanced fluorescence microscopy: nano and micro analysis of chemical and biological systems
• Grantee: Marcelo Henrique Gehlen
• Support Opportunities: Regular Research Grants
• FAPESP's process: 11/08727-1 - Study of organic probes and strategies of DNA fluorescent labelling: from basic photochemistry to super-resolution optical microscopy
• Grantee: Milena Helmer Lauer
• Support Opportunities: Scholarships in Brazil - Doctorate (Direct)
• FAPESP's process: 10/12193-0 - Synthesis of novel fluorescent probes from catalytic processes involving palladium: applications in chemical biology
• Grantee: Roberta Lopes Drekener
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• FAPESP's process: 11/23832-6 - New methodological and mechanistic studies related to the Heck arylations employing arenediazonium salts and synthetic applications
• Grantee: Carlos Roque Duarte Correia
• Support Opportunities: Regular Research Grants