10,15-Dihydro-5H-diindolo[3,2-a:3',2'-c]carbazole

CAS Number 109005-10-9

Chemistry Building Blocks, Heterocyclic Building Blocks, Materials, Monomers

10,15-Dihydro-5H-diindolo[3,2-a:3',2'-c]carbazole MSDS

10,15-Dihydro-5H-diindolo[3,2-a:3',2'-c]carbazole CAS 109005-10-9

10,15-Dihydro-5H-diindolo[3,2-a:3',2'-c]carbazole (triindole)

With a C3 symmetric planar π-extended conjugated structure, 10,15-Dihydro-5H-diindolo[3,2-a:3',2'-c]carbazole finds applications in OLED, OFET and OPV devices.

Specifications | MSDS | Literature and Reviews

10,15-Dihydro-5H-diindolo[3,2-a:3',2'-c]carbazole (triindole), also known as triazatruxene (TAT), CAS number 109005-10-9, is three indoles fused onto a benzene ring at ortho-positions to form a wheel like structure, or it can be considered as two indoles fused to a carbazole structure.

Compared with the carbazole unit, 10,15-dihydro-5H-diindolo[3,2-a:3',2'-c]carbazole is a C3 symmetric planar π-extended conjugated structure which has strong electron-donating capability and usually acts as an electron-donating component on its own or as a part of more complex structures. The triazatruxene structure is an indole cycle-trimer with extended delocalized π-system in which three indole units form an overlapping framework. Due to the disc-like shape of core, triazatruxenes have a high tendency to expand π planes forming columnar supramolecular arrangements. Organic semiconductors based on triazatruxene exhibit high hole mobility and they are most commonly used as hole transporting layer materials due to the strong π-π stacking ability.

Having multiple reactive sites on both the indole nitrogen atoms and the benzene rings, the triazatruxene core is a versatile building block for constructing simple or more complex structures. It is also easy to tune the optical, electronic and morphological properties of the triazatruxene derivatives by functionalizing the core around the rings with different functional groups, i.e. alky chains, electron donating or withdrawing groups. On the other hand, the rigid planar molecular structure of the TAT unit could help to improve the resistance of the materials to photo- and thermal degradation, and to promote effectively charge-carrier transport. Triazatruxene thus has great potential applications as hole transporting or active layer materials in OPVs, OLEDs and OFETs.

General Information

CAS Number	109005-10-9
Chemical Formula	C₂₄H₁₅N₃
Full Name	10,15-Dihydro-5H-diindolo[3,2-a:3',2'-c]carbazole
Molecular Weight	345.41 g/mol
Synonyms	Triazatruxene Triindole 10,15-Dihydro-5H-5,10,15-triazadiindeno[1,2-a:1',2'-c]fluorene
Classification / Family	Indolo-carbazoles, semiconductor synthesis intermediates, Electron donor unit, OLED, OFETs, organic photovoltaics

Chemical Structure

Triazatruxene, 10,15-Dihydro-5H-diindolo[3,2-a:3',2'-c]carbazole, 109005-10-9 — 10,15-Dihydro-5H-diindolo[3,2-a:3',2'-c]carbazole chemical structure, CAS 109005-10-9

Product Details

Purity	>98% (¹H NMR)
Melting Point	350 °C
Appearance	White to yellowish green powder/crystals

MSDS Documentation

10,15-Dihydro-5H-diindolo[3,2-a:3',2'-c]carbazole MSDS Sheet

Literature and Reviews

Air stable organic semiconductors based on diindolo[3,2- a :3′,2′-c]carbazole, A. Cuadrado et al., Org. Electron., 62, 35-42 (2018); DOI:10.1016/j.orgel.2018.07.004.
Triazatruxene-Based Hole Transporting Materials for Highly Efficient Perovskite Solar Cells, K. Rakstys et al., J. Am. Chem. Soc., 137, 51, 16172–16178 (2015); DOI: 10.1021/jacs.5b11076.
Low cost triazatruxene hole transporting material for >20% efficiency perovskite solar cells, A. Connell et al., J. Mater. Chem. C, 7, 5235-5243 (2019); DOI: 10.1039/C8TC04231D.

Dopant-Free Triazatruxene-Based Hole Transporting Materials with Three Different End-Capped Acceptor Units for Perovskite Solar Cells, A. Kil et al., Nanomaterials, 10(5), 936 (2020); DOI: 10.3390/nano10050936.
Benzo[d]imidazole-functionalized triazatruxenes as the emitting materials for solution-processed non-doped OLEDs, Y Zhou et al., Dyes Pigm., 188, 109165 (2021); DOI: 10.1016/j.dyepig.2021.109165.
Triazatruxene: A Rigid Central Donor Unit for a D–A3 Thermally Activated Delayed Fluorescence Material Exhibiting Sub-Microsecond Reverse Intersystem Crossing and Unity Quantum Yield via Multiple Singlet–Triplet State Pairs, P. dos Santos et al., Adv. Sci., 5 (6), 1700989 (2018); DOI: 10.1002/advs.201700989.
Triazatruxene-based materials for organic electronics and optoelectronics, X. Li et al., J. Mater. Chem. C, 4, 10574-10587 (2016); DOI: 10.1039/C6TC03832H.
Designing triazatruxene-based donor materials with promising photovoltaic parameters for organic solar cells, M. Khan et al., RSC Adv., 9, 26402-26418 (2019); DOI: 10.1039/C9RA03856F.
Kinked Star-Shaped Fluorene/ Triazatruxene Co-oligomer Hybrids with Enhanced Functional Properties for High-Performance, Solution-Processed, Blue Organic Light-Emitting Diodes, W. Lai et al., Adv. Funct. Mater., 18 (2), 265-276 (2008); DOI: 10.1002/adfm.200700224.
New exciplex systems composed of triazatruxene donors and N-heteroarene-cored acceptors, Y. Hu et al., Mater. Chem. Front., 4, 2029 (2020); DOI: 10.1039/d0qm00188k.