Anthracene‐Fused Oligo‐BODIPYs: A New Class of π‐Extended NIR‐Absorbing Materials

Abstract

Large π‐conjugated systems are key in the area of molecular materials. Herein, we prepare via AuI‐catalyzed cyclization a series of fully π‐conjugated anthracene‐fused oligo‐BODIPYs. Their structural and optoelectronic properties were studied by several techniques, ranging from X‐ray, UV/Vis, and cyclic voltammetry to transient absorption spectroscopy. As a complement, their electronic structures were explored by means of Density Functional Theory (DFT) calculations. Depending on the size and shape of the π‐conjugated skeleton, unique features—such as face‐to‐face supramolecular organization, NIR absorption and fluorescence as well as strong electron accepting character—were noted. All in all, the aforementioned features render them valuable for technological applications.

Progresses and Perspectives of Near-Infrared Emission Materials with “Heavy Metal-Free” Organic Compounds for Electroluminescence

“…As previously mentioned, the effects on tuning the energy gap are mainly related to the individual molecules without consideration of intermolecular interaction. The intermolecular interaction, for instance, the molecular π-π stacking, hydrogen bonding and charge transfer could also have the influence on altering the band gap of the molecules in the solid states [ 71 , 72 , 73 , 74 , 75 ]. According to the above approaches, researchers have designed and organized NIR luminescent materials.…”

Palladium Catalyzed, Annulative Multiple C‐H Bond Activations of BODIPYs to Access π‐Extended Polycyclic Heteroaromatic Molecules with Deep Red Emissions andSelf‐aggregation Behaviors

“…Shen et al developed an elegant one-pot Suzuki-Miyaura-Knoevenagel reaction [13] from iodinated BODIPYs to provide naphtho[b]-fused BODIPYs. Lately, Tandem Suzuki coupling and gold(I) catalyzed annulation were also able to provide diverse naphtho[b]-fused BODIPYs [14] and oligomers. [15] Nevertheless, these methods are still limited by diversities and efficiency, thus, novel and flexible synthesis of different [b]-aryl-fused BODIPYs remains a great challenge.…”

Gold‐Catalyzed 1,2‐Aryl Shift and Double Alkyne Benzannulation

“…[15][16][17][18][19][20] Among several emblematic examples, a spectacular illustration concerns the synthesis of a polymeric graphene nanoribbon by Chalifoux and co-workers. [21] This reaction has also been used to assemble S-doped [22,23] and Ndoped nanographenes, [24] and, more recently, for the construction of helicenes. [25][26][27][28] Alkyne benzannulation occurs at the free position adjacent to the biaryl linkage leading to the formation of new rings of various sizes.…”