Dibenzocarbazolediimides: Synthesis, Solid Structure, Self‐Assembly Behavior, and Optoelectronic Properties

Abstract

Both planar and nonplanar polycyclic aromatic hydrocarbons (PAHs) have attracted attention owing to their potential applications in optoelectronic materials. Four twist benzopicenediimides with good optoelectronic properties have been reported previously. Following on from this work, four functionalized dibenzocarbazoles have been synthesized and reported herein. The fluorescence quantum yields of these compounds were high in dichloromethane and moderate in the solid state. They have interesting self-assembling behavior and tunable packing motifs in single crystals obtained by introducing different functional groups. Their good optoelectronic properties make them potential candidates for organic devices, bioimaging, and biolabeling.

Imide-Modified Dinaphtho[1,2-b:2′,1′-d]thiophene and Dinaphtho[1,2-b:2′,1′-d]thiophene 13,13-Dioxide: Synthesis and Optoelectronic Properties

“…Compound 1a: Pale yellow solid; 48.8 mg, 91%; mp > 300°C; 1 H NMR (400 MHz, CDCl 3 ) δ H = 9.38 (s, 2H), 8.67−8.69 (d, J = 7.28 Hz, 2H), J = 8.20 Hz,2H),7.93 (t,J = 7.78 Hz,2H) 8,20.4,30.1,40.3,121.1,123.9,125.0,126.8,126.9,128.0,129.5,131.1,133.8,142.1,163.6,163.7;MS (EI) m/z calcd for C 32 H 26 N 2 O 4 S 534.16,found 534.24. Anal.…”

“…All four compounds showed well-resolved absorption bands in the UV region with long-wavelength absorption maxima at 376, 377, 372, and 372 nm in dichloromethane, and a blue shift of around 40 nm was observed in comparison to that of our previously reported analogues II. 8 This may due to stronger electron affinity of sulfur heterocycles. The UV−vis absorption spectra of 1a,b and 2a,b were also measured in thin film.…”

“…7 Recently, we reported a series of dibenzocarbazolediimides (II, Scheme 1), whose lowlying LUMO levels make them potential candidates for n-type organic semiconductor applications. 8 Motivated by the aforementioned advancements and our previous work, we envisaged that introducing two imide groups into dinaphthothiophene I could also make it a potential n-type OSC candidate. We chose dinaphthothiophene I on the basis of the following considerations: packing motifs of such systems; 9 and (2) the S atoms can be easily oxidized to sulfones (or (S,S)-dioxides), which will lead to much lower LUMO levels.…”

Nanocage-Confined Synthesis of Fluorescent Polycyclic Aromatic Hydrocarbons in Zeolite

“…Depending on the orbital gap, PAH molecules exhibit characteristic fluorescence emissions. Often, the orbital gap can be modulated by strong π–π interactions between adjacent PAH molecules. − In some cases, the delocalized electrons over the π-backbone system can exhibit plasmonic characteristics in the visible region. , These optoelectronic properties attract great interest for potential applications of the PAHs to advanced organic devices, such as light-emitting diodes (LEDs), field-effect transistors, and photovoltaic cells. − In adition, they have attracted much attention because they can serve as synthetic precursors for rational synthesis of fullerenes, carbon nanotubes, nanographene, and so on …”

Synthesis, Characterization of Star‐Shaped Analogue with Benzene Core and Three Naphthalene Diimide Side‐Arms

“…Thus naphthalene diimide (NDI) derivatives have been successfully used for n-type electron acceptor, n-semiconductor, intercalator in aromatic donor-acceptor complexes and optoelectronic devices. [16] Based on our previous works, [17][18][19][20][21][22][23][24][25][26] herein, we report the efficient synthesis of star-shaped molecules [27] with benzene core and three NDI side arms, both of which showed desirable electronic properties and can be used as potential n-type materials in electronic devices.…”