Rapid and Selective Electrophilic Trifluoromethylation of the 4,4‐Difluoro‐4‐bora‐3a,4a‐diaza‐ s ‐indacene (BODIPY) Scaffold | Zendy

Santschi Nico | Zendy; Cvengroš Ján | Zendy; Matthey Coraline | Zendy; Otth Elisabeth | Zendy; Antonio Togni and | Zendy

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Rapid and Selective Electrophilic Trifluoromethylation of the 4,4‐Difluoro‐4‐bora‐3a,4a‐diaza‐ s ‐indacene (BODIPY) Scaffold

Author(s) -

Santschi Nico,

Cvengroš Ján,

Matthey Coraline,

Otth Elisabeth,

Antonio Togni and

Publication year - 2014

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201402874

Subject(s) - chemistry , trifluoromethylation , electrophile , bodipy , molar absorptivity , absorbance , quantum yield , derivative (finance) , photochemistry , medicinal chemistry , organic chemistry , chromatography , catalysis , trifluoromethyl , fluorescence , alkyl , physics , quantum mechanics , financial economics , optics , economics

This report deals with the rapid functionalization of the 4,4‐difluoro‐4‐bora‐3a,4a‐diaza‐ s ‐indacene (BODIPY) scaffold by means of electrophilic trifluoromethylation. Subjecting dye 2 to the disclosed protocol led to the successful isolation of 3‐trifluoromethylated derivative 9 . Subsequent comparison of structural and electronic properties allowed for the characterization of changes imparted by the CF 3 group. A diminution in the quantum yield [ Φ F ( 2 ) MeOH = 0.15, Φ F ( 9 ) THF = 0.024] was accompanied by a larger Stokes shift [Δ S ( 2 ) MeOH = 12 nm, Δ S ( 9 ) THF = 54 nm], whereas the molar extinction coefficient at the global absorbance maximum remained largely unaffected [ ϵ ( 2 ) MeOH = 40 × 10 3 M –1 cm –1 , ϵ ( 9 ) THF = 30 × 10 3 M –1 cm –1 ].

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