Description

4,9-Bis(5-bromo-2-thienyl)-2,7-bis(2-ethylhexyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone (CAS: 1320282-67-4) is a high-purity, brominated thienyl-substituted naphthalene diimide (NDI) derivative with the molecular formula C₃₈H₄₀Br₂N₂O₄S₂. This compound features a rigid, planar benzo[lmn][3,8]phenanthroline core functionalized with electron-withdrawing bromothiophene groups and solubilizing 2-ethylhexyl side chains, making it an excellent candidate for optoelectronic and organic semiconductor applications. Its extended π-conjugation and strong electron-accepting properties are ideal for use in organic photovoltaics (OPVs), perovskite solar cells, and n-type organic field-effect transistors (OFETs). The bromine substituents further enable cross-coupling reactions for polymer or small-molecule synthesis. Available in milligram to gram quantities with ≥95% purity (HPLC), this compound is supplied in amber vials under inert gas to ensure stability.

Properties

• CAS Number: 1320282-67-4
• Complexity: 1120
• IUPAC Name: 2,9-bis(5-bromo-2-thienyl)-6,13-bis(2-ethylhexyl)-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaene-5,7,12,14-tetrone
• InChI: InChI=1S/C38H40Br2N2O4S2/c1-5-9-11-21(7-3)19-41-35(43)25-17-24(28-14-16-30(40)48-28)34-32-26(36(44)42(38(34)46)20-22(8-4)12-10-6-2)18-23(27-13-15-29(39)47-27)33(31(25)32)37(41)45/h13-18,21-22H,5-12,19-20H2,1-4H3
• InChI Key: DTTOXIQTFZBNDH-UHFFFAOYSA-N
• Exact Mass: 812.07758
• Molecular Formula: C38H40Br2N2O4S2
• Molecular Weight: 812.7
• SMILES: CCCCC(CC)CN1C(=O)C2=CC(=C3C4=C(C=C(C(=C24)C1=O)C5=CC=C(S5)Br)C(=O)N(C3=O)CC(CC)CCCC)C6=CC=C(S6)Br
• Topological: 131
• Monoisotopic Mass: 810.07963
• Synonyms: 1320282-67-4, 4,9-Bis(5-bromo-2-thienyl)-2,7-bis(2-ethylhexyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone, 4,9-bis(5-bromothiophen-2-yl)-2,7-bis(2-ethylhexyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone, 2,9-bis(5-bromothiophen-2-yl)-6,13-bis(2-ethylhexyl)-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaene-5,7,12,14-tetrone, NDI26-2ThBr, SCHEMBL19821718, Benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone,4,9-bis(5-bromo-2-thienyl)-2,7-bis(2-ethylhexyl)-

Application

This brominated NDI derivative is primarily used as an electron-accepting material in organic electronics, particularly in bulk heterojunction solar cells and OFETs. Its thienyl-bromide groups facilitate further functionalization via Suzuki or Stille coupling for tailored optoelectronic properties. Researchers also exploit its deep LUMO level (−3.8 to −4.0 eV) for air-stable n-type semiconductors. Additionally, it serves as a key intermediate in synthesizing low-bandgap polymers for near-infrared (NIR) photodetectors.

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