Solution-processable perylene diimide-based electron transport materials as non-fullerene alternatives for inverted perovskite solar cells

Abstract

Perylene diimide derivatives with different functional groups (OR) in the bay position were synthesised (PDI-1, OR = OC6H4OMe; PDI-2, OR = OC6H4CH2CH2NHBoc; PDI-3, OR = OC6H4CO2Me) and their optoelectronical properties...

Perylene Diimide-Containing Dynamic Hyper-crosslinked Ionic Porous Organic Polymers: Modulation of Assembly and Gas Storage

“…In this context, perylene diimide (PDI)-based π systems are very interesting owing to their interesting optoelectronic − and spintronic properties with high chemical and thermal stability. Moreover, PDIs are also one of the promising candidates for creating functional soft materials via supramolecular self-assembly. , Furthermore, PDIs are also widely explored as an alternative to fullerenes in solar cells owing to their good electron transporting behavior and spectral coverage in the visible region (400–650 nm). − Owing to these interesting features, PDIs are also utilized as a building block in the synthesis of various POPs such as porous polyimides, − CMPs, and COFs . Hence, introducing PDIs into HCPs not only broadens their synthetic versatility but also introduces interesting functions.…”

Ultrafast Dynamics of Photoinduced Electron Transfer in Bay-Aryl-Substituted Perylene Diimide Derivatives

“…PDIs offer a high absorption coefficient, photostability, and ease of synthetic manipulation, making them suitable for various applications involving electron transfer. − PDI derivatives attached to a heteroleptic iridium complex were used to show single-electron oxidation of a catalyst precursor for water oxidation, and a D–A system involving PDI was demonstrated to show excellent power conversion efficiency in organic solar cells . PDI derivatives have also been used in perovskite solar cells, − two-photon absorption, − and fluorescence upconversion. , Recently, annulation of tetrathiafulvalene (serving as electron donor) at the bay positions of PDI and their electron transfer was studied . In that system, an efficient photoinduced charge-separation process from tetrathiafulvalene to the singlet excited state of PDI was observed in solvents of different polarities.…”

Bay-Substitution of Perylene Bisimides with Bidentate Nucleophiles: The Case of Aryloxide Anions

“…10,12 Furthermore, covalent modifications in the bay region often induce a twisted conformation of the π-conjugated framework, significantly influencing the molecular arrangement in condensates, 13 which is important for their application in the development of novel functional materials. 14,15 Common strategies for functionalizing the bay region of PBIs typically involve introducing halogen or nitro groups, 10 which can act as leaving groups in subsequent nucleophilic aromatic substitutions (S N Ar) with nucleophiles like amines, 16 alcohols, 17−20 or thiols. 21 Notably, bay-functionalized PBIs with alkoxy or aryloxy groups retain the characteristic properties of the starting PBI chromophore, such as high fluorescence quantum yields and photostability, in contrast to amino-substituted PBIs.…”

“…Perylene bisimides (PBIs) are one of the most versatile and extensively employed groups of functional dyes. Their distinctive properties, including remarkable electron affinities, near-unity fluorescence quantum yields, thermal and photochemical robustness, make them an integral part in a wide range of applications in areas such as photocatalysis, organic photovoltaics, − sensing, organic field effect transistors, and OLEDs. , While chemical modifications at the imide position of PBIs typically affect their solubility, , the introduction of substituents at the bay and ortho positions (Scheme a) offers an efficient means to finely tune the optical and redox properties of these dyes. , Furthermore, covalent modifications in the bay region often induce a twisted conformation of the π-conjugated framework, significantly influencing the molecular arrangement in condensates, which is important for their application in the development of novel functional materials. , …”