What is "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. 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 CHMH metalloles

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