3-(Dicyanomethylidene)indan-1-one (2HIC) is electron deficient thus electron withdrawing. It is used as a building block to prepare non-fullerene acceptors (NFAs) such as ITIC, IHIC, IEIC, IXIC for highly efficient organic photovoltaic devices.

3-(Dicyanomethylidene)indan-1-one can also be used for the synthesis of chromophores which exhibit unique photo-physical properties such large second-order optical nonlinearities.

General Information

CAS number	1080-74-6
Chemical formula	C12H6N2O
Molecular weight	194.19 g/mol
Full name	3-(Dicyanomethylidene)indan-1-one
Synonyms	2HIC, 1,1-dicyanomethylene-3-indanone, 2-(3-oxo-2 3-dihydro-1h-inden-1-ylidene)malononitrile, 2-(3-oxo-indan-1-ylidene)-malononitrile, 2-(3-oxoinden-1-ylidene)propanedinitrile
Classification / Family	Malononitrile, Indanone, Monomer and inermediates, ITIC, None-fullerene acceptors (NFAs), NFA-OSCs, printing electronics

Chemical Structure

Product Details

Purity	>98% (by NMR)
Melting point	228 °C (lit.)
Appearance	Pale yellow - Reddish yellow

MSDS Documentation

2HIC MSDS Sheet

Literature and Reviews

1. Efficient DPP Donor and Nonfullerene Acceptor Organic Solar Cells with High Photon‐to‐Current Ratio and Low Energetic Loss, X. Song et al., Adv. Funct. Mater., 1902441 (2019); doi: 10.1002/adfm.201902441
2. Side-Chain Isomerization on an n-type Organic Semiconductor ITIC Acceptor Makes 11.77% High Efficiency Polymer Solar Cells, Y. Yang et al., J. Am. Chem. Soc., 138, 45, 15011-15018 (2016); doi: 10.1021/jacs.6b09110.
3. Terthieno[3,2‐b]Thiophene (6T) Based Low Bandgap Fused‐Ring Electron Acceptor for Highly Efficient Solar Cells with a High Short‐Circuit Current Density and Low Open‐Circuit Voltage Loss, X. Shi et al., Adv. Energy Mater., 8 (12), 1702831 (2018); DIO: 10.1002/aenm.201702831.
4. Second-order nonlinear optical properties of tetrathiafulvalene-π-3-(dicyanomethylidene)indan-1-one chromophores, M. González et al., Tetrahedron Lett., 40 (49), 8599-8602 (1999); doi: 10.1016/S0040-4039(99)01801-8.
5. 1,3-Bis(dicyanomethylidene)indane-Based Second-Order NLO Materials, S. Sun et al., Chem. Mater., 8 (11), 2539-2541 (1996); doi: 10.1021/cm960353q

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To the best of our knowledge the technical information provided here is accurate. However, Ossila assume no liability for the accuracy of this information. The values provided here are typical at the time of manufacture and may vary over time and from batch to batch.

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