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.
|Molecular weight||194.19 g/mol|
|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|
|Purity||>98% (by NMR)|
|Melting point||228 °C (lit.)|
|Appearance||Pale yellow - Reddish yellow|
Literature and Reviews
- 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
- 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.
- 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.
- 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.
- 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
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.