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Description
TCI D2090 2-(Dicyanomethylene)indan-1,3-dione is an organic compound built on an indan-1,3-dione framework that carries a dicyanomethylene group at the 2-position. The combination of two carbonyl groups and two nitrile groups within a single conjugated system makes this molecule one of the strong electron acceptors most frequently used in materials chemistry and organic electronics laboratories. Its role is that of an electron-accepting building block attached to the terminal position of donor molecules to form donor–acceptor architectures, allowing researchers to tune the energy levels, colour, and charge-transfer behaviour of the materials under development in a deliberate, directed way.
The property that makes it a preferred choice is its very high electron deficiency, combined with an active methylene position that participates readily in Knoevenagel condensation with aromatic or heteroaromatic aldehydes. Such reactions generally proceed with a weak base catalyst and give long, stable conjugated systems, often accompanied by a shift of absorption towards the red and near-infrared region. The rigid indandione framework also assists molecular ordering in the solid state, an important factor for charge mobility in the resulting thin films and devices.
In Indonesian laboratories, this building block is typically used in university and institutional research groups working on organic electronic materials, functional dyes, and synthetic methodology. It is commonly ordered in small research quantities for exploratory synthesis, structure–property studies, and the preparation of donor–acceptor compounds that are then characterised spectroscopically. Because it is a specialised building block rather than a bulk reagent, it is usually held in limited amounts and handled within organic synthesis and materials chemistry workflows.
Laboratory Applications
- Donor–acceptor material synthesis: serves as the terminal electron-accepting unit that sets the energy levels and charge-transfer character of newly designed conjugated molecules.
- Knoevenagel condensation chemistry: the active methylene position reacts readily with aromatic and heteroaromatic aldehydes under weak base catalysis to extend conjugation.
- Organic electronics research: the strong electron deficiency and rigid framework support studies of charge mobility and solid-state molecular ordering in functional films.
- Functional dye and near-infrared chromophore development: extended conjugation from condensation products shifts absorption towards the red and near-infrared region for optical studies.
- Structure–property investigations: allows researchers to vary the donor partner systematically and correlate molecular design with colour, energy levels, and charge-transfer behaviour.
Specifications
- Brand: TCI
- CAS number: 16954-74-8
- Chemical name: 2-(Dicyanomethylene)indan-1,3-dione
- Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
- Pack sizes: available in standard research-scale packaging as supplied by the manufacturer
- Storage: keep in the original tightly closed container, protected from moisture and light
Handling and Storage
Store the material in its original tightly closed container, in a cool, dry, and well-ventilated area away from direct sunlight, moisture, and sources of ignition. Amber glass or the manufacturer's original packaging is suitable for keeping the compound protected from light and humidity. Handle in a fume hood using standard laboratory personal protective equipment, including safety goggles, a laboratory coat, and chemical-resistant gloves, and avoid generating dust when weighing. Keep the compound away from strong bases and strong oxidising agents, close the container promptly after use, and dispose of residues and contaminated materials in accordance with applicable chemical waste procedures and the manufacturer's safety data sheet.
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