Core-Extended Terrylene Diimide on the Bay Region: Synthesis and Optical and Electrochemical Properties

Abstract

Two novel core-extended terrylene diimides on the bay region (CETDIs) were synthesized via annulation of the four additional ethylene units or benzene units on the bay region of the terrylene diimide core. The optical and electrochemical properties of the two compounds were investigated. These CETDIs exhibited broad absorption spectra with high extinction coefficients, which span a wide range in the ultraviolet and visible spectrum from 300 to 700 nm. Furthermore, the redox process of the CETDIs increased from two waves to four waves, and the lowest unoccupied molecular orbital (LUMO) levels were enhanced from -4.00 to -3.59 eV.

The efficient synthesis of N-fused coronene analogs and a related polyimide with near-infrared absorption

“…The optical band gap, which was calculated from the absorption edge of the film spectrum, was 1.3 eV. A low band gap is required for semiconductors, [8][9][10][11] nearinfrared applications 12,13 and solar cells. 21,22 The cyclic voltammetry analysis of FCTI-Cl determined that the lowest unoccupied molecular orbital and the highest occupied molecular orbital levels were 3.75 and 5.38 eV, respectively.…”

“…7 To produce carbon derivatives of coronene, the transition metal-catalyzed coupling of bromo-substituted perylene and other aromatic moieties is popular. [8][9][10][11] The fused cyclic structure of coronene is prepared through a pericyclic reaction, and the thermal coupling reaction between the perylene imides and dienophiles followed by the in situ aromatization produces the coronene structure. 12,13 Electron-deficient coronene octacarboxylic tetraimides have been developed for columnar liquid crystals.…”

“…4,5 Many studies of coronene analogs have focused on their applications in photovoltaic devices, organic field effect transistors and liquid crystals. [8][9][10][11] These applications take advantage of the electronic properties of flat molecules that allow for pi-overlap. Z Wang and K Müllen examined the extension of the aromatic core on a perylene bay.…”

“…Z Wang and K Müllen examined the extension of the aromatic core on a perylene bay. [8][9][10][11] Significant optical changes were achieved by extending the length. Heterocyclic extensions, such as the N-and S-cycle, were used for their molecular recognition or optical absorption properties.…”

“…Heterocyclic extensions, such as the N-and S-cycle, were used for their molecular recognition or optical absorption properties. [8][9][10][11][12][13][14] H Langhals et al 12,13 reported a triazolinedione adduct of perylene imides, which absorbs near-infrared light. The introduction of electron-donating nitrogen to a perylene imide often involves a strong bathochromic shift.…”