N3

N3, small molecule non-fullerene acceptor and Y6 family member

Exhibits optimum properties of domain size and crystallinity resulting in excellent device performance

N3 (Y6-N3) is another non-fullerene acceptor that belongs to the Y6 family. The only difference between N3 and Y6 is that the location of the branching points on the inside branched side chains and a slightly longer chain (3-ethylheptyl) for N3, while Y6 has classic 2-ethylhexyl branched side chains. With 3rd-position branched alkyl chains, N3, exhibits optimum properties in terms of domain size, crystallinity, and more dominant face-on orientation of the π-π stacking.

difference between N3 and Y6 in structure — The difference between N3 and Y6

Non-fullerene acceptor N3 has a clear solid-state aggregation transition at 82 °C. The shifting of the branching position of the alkyl chains increases the solubility of the molecule significantly from 40 mg/mL for Y6 to 64 mg/mL for N3 in chloroform.

Optimised photovoltaic devices using a binary acceptor system with N3:PC71BM as the acceptors and PBDB-T-2F (PM6) as the polymer donor shows efficient device performance with power conversion efficiencies (PCEs) of up to 16.74% (device 1), and 18.69% while D18-Cl:N3:PC61BM (1:1.4:0.1) is used as the active layer materials (device 2).

Device structure 1: ITO/PEDOT:PSS/PM6:N3:PC71BM/PNDIT-F3N/Ag.

Thickness (nm)	V_OC(V)	J_SC (mA cm^-2)	FF (%)	PCE (%)
110	0.850	25.71	76.6	16.74

Device structure 2: ITO/PEDOT:PSS/D18-Cl:N3:PC61BM (1:1.4:0.1)/PDIN/Ag.

Thickness (nm)	V_OC(V)	J_SC (mA cm^-2)	FF (%)	PCE (%)
114	0.849	28.22	78.0	18.69

Y6 (BTP-4F) from Ossila was used in the high-impact paper (IF 29.37), Triplet-Charge Annihilation in a Small Molecule Donor: Acceptor Blend as a Major Loss Mechanism in Organic Photovoltaics, J. Marin-Beloqui et al., Adv. Energy Mater., 2100539 (2021); DOI: 10.1002/aenm.202100539.

Chemical Structure

Literature and Reviews

Alkyl Chain Tuning of Small Molecule Acceptors for Efficient Organic Solar Cells, K. Jiang et al., Joule, 3 (12); 3020-3033 (2019); DOI: 10.1016/j.joule.2019.09.010.
18.69% PCE from organic solar cells, K. Jin et al., J. Semicond., 42(6), 060502 (2021); DOI: 10.1088/1674-4926/42/6/060502.
Low Temperature Aggregation Transitions in N3 and Y6 Acceptors Enable Double-Annealing Method That Yields Hierarchical Morphology and Superior Efficiency in Nonfullerene Organic Solar Cells, Y. Qin et al., Adv. Funct. Mater., 2005011 (2020); DOI: 10.1002/adfm.202005011.
Thermoplastic Elastomer Tunes Phase Structure and Promotes Stretchability of High-Efficiency Organic Solar Cells, Z. Peng et al., Adv. Mater., 2106732 (2021); DOI: 10.1002/adma.202106732.
Modulation of Morphological, Mechanical, and Photovoltaic Properties of Ternary Organic Photovoltaic Blends for Optimum Operation, Z. Peng et al., Adv. Energy Mater., 2003506 (2021); DOI: 10.1002/aenm.202003506.
Self-assembled Monolayer Enables Hole Transport Layer-free Organic Solar Cells with 18% Efficiency and Improved Operational Stability, Y. Lin et al., ACS Energy Lett., 5, 9, 2935–2944 (2020); DOI: 10.1021/acsenergylett.0c01421..

General Information

CAS Number	N/A
Chemical Formula	C₈₄H₉₀F₄N₈O₂S₅
Purity	>99% (¹H NMR)
Full Name	2,2'-((2Z,2'Z)-((12,13-bis(3-ethylheptyl)-3,9-diundecyl-12,13-dihydro-[1,2,5]thiadiazolo[3,4-e]thieno[2'',3'':4',5']thieno[2',3':4,5]pyrrolo[3,2-g]thieno[2',3':4,5]thieno[3,2-b]indole-2,10-diyl)bis(methanylylidene))bis(5,6-difluoro-3-oxo-2,3-dihydro-1H-indene-2,1-diylidene))dimalononitrile
Molecular Weight	1479.98 g/mol
HOMO / LUMO	HOMO = -5.65 eV, LUMO = -4.10 eV [1]
Synonyms	Y6N3, Y6-N3
Classification / Family	NFAs, n-type non-fullerene electron acceptors, Organic semiconducting materials, Low band-gap small molecule, Small molecular acceptor, Organic photovoltaics, Polymer solar cells, NF-PSCs