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Sigma-Aldrich

6,12-Bis(2,4,6-trimethylphenyl)indeno[1,2-b]fluorene

97% (HPLC)

Synonym(s):

6,12-Dimesitylindeno[1,2-b]fluorene

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About This Item

Empirical Formula (Hill Notation):
C38H32
CAS Number:
1374154-86-5
Molecular Weight:
488.66
UNSPSC Code:
12352103
PubChem Substance ID:
329768315

Assay

97% (HPLC)

form

powder

Orbital energy

HOMO -5.78 eV 
LUMO -3.56 eV 

SMILES string

CC(C=C1C)=CC(C)=C1C2=C3C(C=CC=C3)=C(C2=C4)C=C5C4=C(C=CC=C6)C6=C5C7=C(C)C=C(C)C=C7C

InChI

1S/C38H32/c1-21-15-23(3)35(24(4)16-21)37-29-13-9-7-11-27(29)31-20-34-32(19-33(31)37)28-12-8-10-14-30(28)38(34)36-25(5)17-22(2)18-26(36)6/h7-20H,1-6H3

InChI key

RVYZMPWWAUBURT-UHFFFAOYSA-N

General description

6,12-Bis(2,4,6-trimethylphenyl)indeno[1,2-b]fluorene is a conjugated polycyclic hydrocarbon which has indeno[1,2-b]fluorene as the skeleton. It has a 6−5−6−5−6 fused ring system with small band gap absorption and biradicaloid properties. It can be potentially used in organic electronics based applications.

Application

6,12-Bis(2,4,6-trimethylphenyl)indeno[1,2-b]fluorene can be potentially used in the fabrication of ambipolar semiconductors, organic light emitting diodes (OLEDs), organic field effect transistors (OFETs), and organic photovoltaic (OPV) devices.
n-type electron-accepting organic semiconductor for Organic Field Effect Transistor (OFET) applications

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Indeno [1, 2-b] fluorenes: Fully Conjugated Antiaromatic Analogues of Acenes.
Chase DT, et al.
Angewandte Chemie (International Edition in English), 123(5), 1159-1162 (2011)
Isomeric indacenedibenzothiophenes: synthesis, photoelectric properties and ambipolar semiconductivity.
Ren L, et al.
Journal of Material Chemistry C, 4(23), 5202-5206 (2016)
Toward tetraradicaloid: The effect of fusion mode on radical character and chemical reactivity.
Hu P, et al.
Journal of the American Chemical Society, 138(3), 1065-1077 (2016)
Daniel T Chase et al.
Journal of the American Chemical Society, 134(25), 10349-10352 (2012-06-16)
Herein we report the synthesis and characterization of a series of 6,12-diarylindeno[1,2-b]fluorenes (IFs). Functionalization with electron donor and acceptor groups influences the ability of the IF scaffold to undergo two-electron oxidation and reduction to yield the corresponding 18- and 22-π-electron
Electron-accepting 6, 12-diethynylindeno [1, 2-b] fluorenes: synthesis, crystal structures, and photophysical properties.
Chase DT, et al.
Angewandte Chemie (International Edition in English), 50(47), 11103-11106 (2011)

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