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Azadipyrromethene‐Based Near‐Infrared Dyes: Effect of Thienylethynyl Substitution at the Distal and Proximal Phenyl Groups
Author(s) -
Daddario Cassie M.,
Han Qi,
Zeller Matthias,
Sauvé Geneviève
Publication year - 2015
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201500348
Subject(s) - chemistry , zinc , cyclic voltammetry , molecule , chelation , infrared spectroscopy , absorption spectroscopy , solubility , absorption (acoustics) , phenyl group , medicinal chemistry , polymer chemistry , photochemistry , inorganic chemistry , alkyl , organic chemistry , electrochemistry , electrode , physics , quantum mechanics , halogen , acoustics
Azadipyrromethene (ADP) ligands substituted with thienylethynyl substituents either at the distal phenyl groups H(CD1) or the proximal phenyl groups H(CD2) were synthesized and characterized. The thienyl groups have a hexyl group at the third position to improve solubility in organic solvents and prevent homocoupling of the ethynylthiophene reactants. To further tune the opto‐electronic properties, the substituted ADPs were coordinated with BF 2 + and Zn II . Absorption spectroscopy shows that the thienylethynyl substitutions redshift the absorption spectra of the dyes, with a larger shift when the substituents are added on the proximal phenyl groups. Cyclic voltammetry experiments show that the substitutions stabilize the anion and dianion. The reduction potentials for the modified ligands (or zinc chelates) were not affected by the placement of the thienylethynyl groups. Preliminary studies of blends of the new molecules with poly(3‐hexylthiophene) (P3HT) suggest that the zinc(II) chelates have potential as electron acceptors for organic solar cells.