1071985-20-0Relevant academic research and scientific papers
Tuning the Properties of Azadipyrromethene-Based Near-Infrared Dyes Using Intramolecular BO Chelation and Peripheral Substitutions
Jimenez, Jayvic C.,Zhou, Zehao,Rheingold, Arnold L.,Parker, Shane M.,Sauvé, Geneviève
, p. 13320 - 13331 (2021)
Tetraphenylazadipyrromethenes (ADPs) are attractive near-infrared (NIR) dyes because of their simple synthesis and exceptional optical and electronic properties. The typical BF2 and less explored intramolecular BO coordination planarize the molecule, making them promising π-conjugated materials for organic electronic applications. However, their use has been mostly limited to vacuum-deposited devices. To improve the properties, we synthesized and characterized a series of ADP complexes and used density functional theory calculations to further explain the properties. Hexyloxy solubilizing groups increase the complexes' solubility in organic solvents and enable film formation from solution. Phenylethynyls at the pyrrolic positions extend πconjugation, red-shift absorption and emission peaks, and increase the ionization potential (IP) and electron affinity. When the properties of complexes with hexyloxy and phenyethynyl substitutions are compared, the BO complex is more planar and has a smaller IP than the corresponding BF2 complex because of increased electron density on the proximal phenyls. The BO complex has an unusual combination of properties: a solution λmax of 781 nm, emission at 805 nm, a small Stokes shift, and a quantum yield of 6%. It forms transparent films with a low optical gap of 1.22 eV. This new complex is a promising candidate for transparent solar cells and NIR photodetectors.
The synthesis and structures of arene-substituted azadipyrromethenes
Chanawanno, Kullapa,Hasheminasab, Abed,Engle, James T.,Ziegler, Christopher J.
, p. 276 - 281 (2015/10/19)
We present the synthesis of several azadipyrromethenes with four peripheral arene units which can be readily generated via the well-established chalcone synthetic method. The stability and yields of these azadipyrromethenes is highly dependent on the nature of the arene substituent, with the bis-pyridine systems exhibiting the highest degree of instability. The structures of several of the compounds and their BF2 adducts are presented; intramolecular hydrogen bonding is observed in the free base ADPMs. We also present a study into the absorption and emission properties of the ADPMs and their BF2 adducts and observe that they are also highly dependent on the identity of the substituents.
B, O-chelated azadipyrromethenes as near-IR probes
Loudet, Aurore,Bandichhor, Rakeshwar,Burgess, Kevin,Palma, Aniello,McDonnell, Shane O.,Hall, Michael J.,O'Shea, Donal F.
supporting information; experimental part, p. 4771 - 4774 (2009/05/31)
(Chemical Equation Presented Complementary synthetic routes to a new class of near-IR fluorophores are described. These allow facile access (four synthetic steps) to the core fluorophore and substituted derivatives with emissions between 740 and 780 nm in good quantum yields.
