Conjugated polymers based on 1,8‐naphthalene monoimide with high electron mobility

Abstract

1,4,8,9‐Naphthalene diimides (NDIs) with strong electron accepting ability and high stability are excellent building blocks for semiconductor polymers. However, 1,8‐naphthalene monoimide (NMI) with similar structure and energy levels as that of NDI has never been used to construct conjugated polymers because of synthetic difficulty. Herein, 3,6‐dibromo‐NMI (DBNMI) with bulky alkyl groups was obtained effectively in a four‐step synthesis, and three donor‐acceptor (D‐A) type conjugated polymers based on NMI were firstly prepared. These polymers have strong absorption in the range of 300–600 nm, low LUMO level of 3.68 eV, and moderate bandgaps of 2.18 eV. Space charge limiting current measurements indicate these polymers are typical electron transporting materials, and the highest electron mobility is up to 5.8 × 10−3 cm2 V−1 s−1, which is close to the star acceptor based on NDI (N2200, 5.0 × 10−3 cm2 V−1 s−1). © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018, 56, 276–281

Marked Passivation Effect of Naphthalene‐1,8‐Dicarboximides in High‐Performance Perovskite Solar Cells

“…These polyaromatic chromophores usually possess low-lying LUMO levels, strong absorption, and high electron mobility. [39,40] To validate the combination of different functional groups, we add different functional groups (protonic OH and non-protonic CN) opposite to the electron-withdrawing imide rings across the naphthalene and perylene spacer, respectively. Then, the two multifunctional polyaromatic molecules, 4-hydroxybiphenylsubstituted NMI (4OH-NMI), [41] and cyanide-substituted PMI (9CN-PMI) [42] (Figure S1b,d, Supporting Information), are added to the perovskite precursor solution as the passivator and crystal growth-controlling agent.…”

Subphthalocyanine Triimides: Solution Processable Bowl-Shaped Acceptors for Bulk Heterojunction Solar Cells

“…Compared to parent SubPc, introduction of imide groups lowered LUMO energy levels by 0.35−0.42 eV, due to their strong electron-withdrawing properties. 27 Geometries of aromatic cores of these acceptors were optimized with Gaussian 09 program, density functional theory (DFT) method, with basic set of B3LYP/6-311G (d, p). 28 Their absorption and band gaps were also calculated.…”

“…Above energy levels could match with many donors in BHJOSCs. Compared to parent SubPc, introduction of imide groups lowered LUMO energy levels by 0.35–0.42 eV, due to their strong electron-withdrawing properties …”

Luminescent Imidazolium Salts as Bright Multi‐Faceted Tools for Biology

“…In order to study the cytotoxic potential of a radio-iodinated IM derivative on several cancer cell lines compared to healthy cells, Er et al [49] added iodine-131 on an IM bearing a 1,8naphthalene monoimide fragment (Figure 10) known for its fluorescence properties. [50] The latter IM derivative is also currently investigated for its excellent cytotoxic and antibacterial power. [51,52] In this article, the fragment's fluorescence has not been exploited for imaging purpose but could lead to a complementary study.…”