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 intermediates, 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
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