Abstract
Organic semiconductors are usually polycyclic aromatic hydrocarbons and their analogs containing heteroatom substitution. Bioinspired materials chemistry of organic electronics promises new charge transport mechanism and specific molecular recognition with biomolecules. We discover organic semiconductors from deoxyribonucleic acid topoisomerase inhibitors, featuring conjugated backbone decorated with hydrogen-bonding moieties distinct from common organic semiconductors. Using ellipticine as a model compound, we find that hydrogen bonds not only guide polymorph assembly, but are also critical to forming efficient charge transport pathways along π−conjugated planes when at a low dihedral angle by shortening the end-to-end distance of adjacent π planes. In the π−π stacking and hydrogen-bonding directions, the intrinsic, short-range hole mobilities reach as high as 6.5 cm2V−1s−1 and 4.2 cm2V−1s−1 measured by microwave conductivity, and the long-range apparent hole mobilities are up to 1.3 × 10–3 cm2V−1s−1 and 0.4 × 10–3 cm2V−1s−1 measured in field-effect transistors. We further demonstrate printed transistor devices and chemical sensors as potential applications.
Highlights
Organic semiconductors are usually polycyclic aromatic hydrocarbons and their analogs containing heteroatom substitution
Current molecular designs of high-performance organic semiconductors usually conform to polycyclic aromatic hydrocarbons and their analogs containing heteroatom substitution;[4] electrons are delocalized over extended π-conjugated system, imparting charge mobility when subjected to the electric field
We note that organic semiconductors with wide bandgaps and uncompromised electronic performance have been pursued owing to their improved air stability, reduced photooxidation and light sensitivity, and high transparency to visible light[28,29]
Summary
Organic semiconductors are usually polycyclic aromatic hydrocarbons and their analogs containing heteroatom substitution. We discover that a group of anticancer plant alkaloids and their derivatives, known as DNA topoisomerase I and II inhibitors, can serve as a promising source for mining solution printable, high-performance organic semiconductors These compounds interact with DNA via π−π stacking and hydrogen bonding, and thereby intercalate between the DNA base pairs or bind with topoisomerase–DNA complex to inhibit DNA replication. Required by such anticancer properties, these compounds often possess highly co-planar conjugated backbone decorated with hydrogen-bond donors and acceptors; both features are conducive to intermolecular electronic coupling for efficient charge transport in solid-state assemblies. We further demonstrate application of this biological semiconductor in solution printed organic field-effect transistor (OFET) devices and chemical sensors
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