Metallole

Metalloles are derivatives of cyclopentadiene in which the carbon atom at position 5, the saturated carbon, is replaced by a heteroatom. In contrast to its parent compound, the numbering of the metallole starts at the heteroatom. Some of these compounds are described as organometallic compounds, but in the list below quite a number of metalloids are present too.[1] Many metalloles are fluorescent and are used in organic light-emitting diodes (OLEDs) and other applications. Metalloles, which can also be viewed as structural analogs of pyrrole, include:

Calculated geometry and inversion barrier energy E for some C4H4MH metalloles[2]
Name M d(M-C), Åd(M-H), Åα(C-M-C), °E, kJ/mol
PyrroleN 1.37 1.01 1100
PhospholeP 1.81 1.425 90.567
Arsole As1.94 1.53 86125
StiboleSb 2.14 1.725 80.5 160
BismoleBi 2.24 1.82 78 220

References

  1. Tracy, Henry J.; Mullin, Jerome L.; Klooster, Wim T.; Martin, James A.; Haug, Judith; Wallace, Scott; Rudloe, Isaac; Watts, Kimberly (2005). "Enhanced Photoluminescence from Group 14 Metalloles in Aggregated and Solid Solutions". Inorganic Chemistry 44 (6): 2003–2011. doi:10.1021/ic049034o. PMID 15762727.
  2. Pelzer, Silke; Wichmann, Karin; Wesendrup, Ralf; Schwerdtfeger, Peter (2002). "Trends in Inversion Barriers IV. The Group 15 Analogous of Pyrrole". The Journal of Physical Chemistry A 106: 6387. doi:10.1021/jp0203494.


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