π-Conjugated molecules with small highest occupied molecular orbital (HOMO)−lowest unoccupied molecular orbital (LUMO) energy gaps (ΔE H−L ) have been extensively studied because of their unique optoelectronic properties. Although the expansion of πconjugation is one of the well-known approaches for designing molecules with small ΔE H−L values, such an approach inevitably gives large πconjugated molecules sometimes suffering from synthetic difficulty and low solubility toward organic solvents. To develop relatively small donor− acceptor molecules with small ΔE H−L values, we have designed and synthesized π-conjugated zwitterions composed of electron-donating anions, such as phenoxide and anthroxide, and electron-accepting cations, such as pyridinium and acridinium. The energy difference between the HOMO of the anion and the LUMO of the cation (ΔE D−A ) and the interplanar angle between them (φ DA ) have a crucial effect on ΔE H−L , and hence, on the electronic structures and optoelectronic properties of these zwitterions. The zwitterions with small ΔE D−A and large φ DA have a small ΔE H−L of ca. 1 eV and show amphoteric redox properties and near-infrared (NIR) electronic absorption exceeding λ = 1000 nm. The NIR absorption responds to solvent polarity, temperature, and acid addition. This molecular design will generate small π-conjugated donor−acceptor molecules with small ΔE H−L values.

A three-step transformation consisting of 1) addition of electrochemically generated iodosulfonium ions to vinylarenes to give (1-aryl-2-iodoethoxy)sulfonium ions, 2) nucleophilic substitution by subsequently added aromatic compounds to give 1,1-diaryl-2-iodoethane, and 3) elimination of HI with a base to give 1,1-diarylethenes was developed. The transformation serves as a powerful metal- and chemical-oxidant-free method for alkenyl C-H/aromatic C-H cross-coupling.

Athree-step transformation consisting of 1) addition of electrochemically generated iodosulfonium ions to vinylarenes to give (1-aryl-2-iodoethoxy)sulfonium ions,2 )nucleophilic substitution by subsequently added aromatic compounds to give 1,1-diaryl-2-iodoethane,a nd 3) elimination of HI with ab ase to give 1,1-diarylethenes was developed. The transformation serves as ap owerful metal-and chemicaloxidant-free method for alkenyl CÀH/aromatic CÀHc rosscoupling. Scheme 1. Synthesis of diarylethylene. Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under https://doi.org/10. 1002/anie.201807592. Scheme 2. Alkenyl CÀH/aromatic CÀHcross-couplingvia b-iodoalkoxysulfonium ion. FG:afunctionalg roup.

We propose a novel software-based optical sampling scheme for time-of-flight light detection and ranging using pseudo-random binary sequences. Temporal resolution of 1.1 ps, corresponding to a ranging resolution of 165um can be achieved.