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Title: Tuning the photophysical properties of BODIPY dyes through extended aromatic pyrroles

Three new BODIPY dyes have been synthesized by a two-step synthetic route. Here, this expands the series to nine different BODIPY dyes by this method. Naphtha[1,2-c]pyrrole was combined with 1-pyrenecarboxaldehyde to give a symmetric dipyrrin followed by reaction with boron trifluoride to give a symmetric highly conjugated BODIPY dye. Expanding this synthetic route to a more conjugated pyrrole fluorantho[2,3-c]pyrrole was combined with 1-pyrenecarboxaldehyde followed by reaction with boron trifluoride to give the asymmetric BODIPY dye (9). Dyes with the more highly conjugated fluoranthopyrrole resulted in a bathochromic shift of ca. 50 nm in the electronic absorption and showed greater stability of the LUMO energy, as determined by electrochemical measurements, compared to their naphthapyrrole analogs. All of the dyes synthesized by this method display molar absorptivities greater than 100 000 M -1 cm -1 with photoluminescence quantum efficiencies of 0.8–1.0. Excited state lifetimes of the dyes in dichloromethane are modest, ranging from 3.2 ns to 4.3 ns.
Authors:
 [1] ;  [1] ;  [1] ;  [2] ;  [2]
  1. Univ. of Dayton, Dayton, OH (United States). Dept. of Chemistry
  2. Univ. of North Carolina, Chapel Hill, NC (United States). Dept. of Chemistry
Publication Date:
Grant/Contract Number:
SC0001011
Type:
Accepted Manuscript
Journal Name:
RSC Advances
Additional Journal Information:
Journal Volume: 7; Journal Issue: 1; Journal ID: ISSN 2046-2069
Publisher:
Royal Society of Chemistry
Research Org:
Univ. of North Carolina, Chapel Hill, NC (United States)
Sponsoring Org:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
OSTI Identifier:
1425204