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Two‐Step Synthetic Route toward Asymmetric and Symmetric Boron Dipyrromethenes: Synthesis, Optical Properties, and Electrochemistry
Author(s) -
Swavey Shawn,
Coladipietro Michael,
Burbayea Aliah,
Krause Jeanette A.
Publication year - 2016
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.201600787
Subject(s) - chemistry , aldehyde , pyrrole , bodipy , oxidizing agent , electrochemistry , catalysis , boron , photochemistry , solvent , combinatorial chemistry , organic chemistry , electrode , physics , quantum mechanics , fluorescence
A two‐step synthetic route toward BODIPY dyes is accomplished by reaction of the readily available naphtho[1,2‐ c ]pyrrole with various aldehydes followed by coordination of BF 2 . Synthesis of the dipyrromethene is achieved by simply heating the pyrrole and aldehyde at moderate temperatures for less than 30 min. In addition to the absence of solvent this reaction does not require an acid catalyst or an oxidizing agent to achieve the dipyrromethene. Investigation of various aldehydes by this method suggests that the choice of aldehyde plays a role in the formation of either symmetric or asymmetric BODIPYs. The dyes have exceptionally high molar absorptivities (> 1 m –1 cm –1 ) in the far visible region of the electromagnetic spectrum with intense emission and high quantum efficiency.