Metallole
Appearance
Metalloles are derivatives of cyclopentadiene in which the carbon atom at position 5, the saturated carbon, is replaced by an 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:
Name | M | d(M-C), Å | d(M-H), Å | α(C-M-C), ° | E, kJ/mol |
---|---|---|---|---|---|
Pyrrole | N | 1.37 | 1.01 | 110 | 0 |
Phosphole | P | 1.81 | 1.425 | 90.5 | 67 |
Arsole | As | 1.94 | 1.53 | 86 | 125 |
Stibole | Sb | 2.14 | 1.725 | 80.5 | 160 |
Bismole | Bi | 2.24 | 1.82 | 78 | 220 |
- Arsole, a moderately-aromatic arsenic analog
- Bismole, a bismuth analog
- Borole, a boron analog
- Furan (oxole), an oxygen analog
- Gallole, a gallium analog
- Germole, a germanium analog
- Phosphole, a phosphorus analog
- Plumbole, a lead analog
- Pyrrole (azole), a nitrogen analog
- Selenophene, a selenium analog
- Silole, a silicon analog
- Stannole, a tin analog
- Stibole, an antimony analog
- Tellurophene, a tellurium analog
- Thiophene, a sulfur analog
- Titanacyclopentadiene, a titanium analog
- Zirconacyclopentadiene, a zirconium analog
References
- ^ 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. doi:10.1021/ic049034o. PMID 15762727.
- ^ 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.