Structure–Property Relationship of Macrocycles in Organic Photoelectric Devices: A Comprehensive Review

Abstract

Macrocycles have attracted significant attention from academia due to their various applications in organic field-effect transistors, organic light-emitting diodes, organic photovoltaics, and dye-sensitized solar cells. Despite the existence of reports on the application of macrocycles in organic optoelectronic devices, these reports are mainly limited to analyzing the structure–property relationship of a particular type of macrocyclic structure, and a systematic discussion on the structure–property is still lacking. Herein, we conducted a comprehensive analysis of a series of macrocycle structures to identify the key factors that affect the structure–property relationship between macrocycles and their optoelectronic device properties, including energy level structure, structural stability, film-forming property, skeleton rigidity, inherent pore structure, spatial hindrance, exclusion of perturbing end-effects, macrocycle size-dependent effects, and fullerene-like charge transport characteristics. These macrocycles exhibit thin-film and single-crystal hole mobility up to 10 and 26.8 cm2 V−1 s−1, respectively, as well as a unique macrocyclization-induced emission enhancement property. A clear understanding of the structure–property relationship between macrocycles and optoelectronic device performance, as well as the creation of novel macrocycle structures such as organic nanogridarenes, may pave the way for high-performance organic optoelectronic devices.

Structural determination, characterization and computational studies of doped semiconductors base silicon phthalocyanine dihydroxide and dienynoic acids

“…SiPc(OH) 2 has been little studied as an organic semiconductor in an active layer, and its structure with symmetrical ligands can display interesting optical and electronic properties. For the manufacture of the active layer, an innovative dopant of SiPc(OH) 2 which behaves as a p-type semiconductor [ 18 ] is proposed: the (2E, 4Z) dienynoic acids that show an n-type semiconductor behaviour. Doping is expected to improve the efficiency of the device by modifying the conductive properties of phthalocyanine and allowing more efficient charge transport in SiPc(OH) 2 -DAc films.…”

A donor–acceptor cross-conjugated phenazine macrocycle with a large Stokes shift for sensing transition metal ions with “turn-on” fluorescence

“…Organic conjugated macrocycles (OCMCs) have garnered substantial attention in the last decade because of their unique optoelectronic properties and symmetric terminal-less structures 1–7 and have been applied in many fields, such as OLEDs, 8,9 OFETs, 10,11 solar cells, 12,13 and fluorescence sensors. 14–16 OCMCs are mainly divided into two categories based on their linkage positions: cyclo- para -phenylenes (CPPs) 17 and cyclo- meta -phenylenes (CMPs).…”