Organic Chemistry I Lab

AboutAbout the lab

From Hokkaido University, the world's best in organic chemistry.

The Organic Chemistry I Lab designs and synthesizes organic compounds that do not exist in nature.
The lab deliberately designs molecules whose color and properties change in response to stimuli such as light, heat, and electric potential.
It also tests the limits of bonds and structures experimentally, including setting a world record for the length of a carbon–carbon single bond.
It continues research on responsive molecules that lead to molecular electronics and display functions.

ResearchResearch themes

The lab designs and synthesizes organic compounds with physical and biological functions. Centered on redox-responsive systems aimed at molecular electronics and on the creation of chirality, it searches for new functions.

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The world's longest carbon–carbon single bond↗

The standard length of a carbon–carbon single bond is 1.54 Å, but bulky substituents on both sides stretch it through repulsion. It was once predicted that a bond longer than 1.75 Å could not exist. Through precise molecular design, the lab experimentally demonstrated a 1.806 Å bond, the world's longest single bond in a neutral compound, and continues to search for "super bonds" exceeding 1.8 Å.

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Responsive molecules that answer when called↗

Molecules that switch between two states in response to an external stimulus, changing color and other properties, are called "responsive molecules." The lab continues work on electrochromic systems, in which color changes in response to a change in electric potential, and designs molecules that accept multiple stimuli or give outputs other than color change, aiming toward single-molecule memory and molecular logic operators.

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Nitrogen heterocycles that give stable radicals↗

Radicals, which have an unpaired electron, are usually short-lived species, but they can live longer when the electron is delocalized over heteroatoms and π-conjugated systems. Using fused nitrogen heterocyclic compounds, for which no synthesized examples existed before, as the subject, the lab makes stable ion radicals and neutral radicals and studies their near-infrared light absorption and electrical conductivity.

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Molecules that respond to different stimuli in solution and in the solid state↗

The lab has made molecules that show different responses to different stimuli in solution and in the solid state. Tetraaryl anthraquinodimethane changes color through redox in solution, while in the solid state, grinding converts the crystal to an amorphous form and changes its luminescence. White luminescence has also been observed in a derivative with methoxyphenyl groups.

VoicesStudent voices

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