3-(Dicyanomethylidene)indan-1-one


Order Code: B541
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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 

Product Details

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

ic-2h, 1080-74-6
Chemical structure of 3-(Dicyanomethylidene)indan-1-one (2HIC), CAS# 1080-74-6.

 

Applications

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.

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

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.