TY - JOUR

T1 - Subphthalocyanine–triangulene dyads

T2 - Property tuning for light-harvesting device applications

AU - Rasmussen, Mads Georg

AU - Jespersen, Malte Frydenlund

AU - Blacque, Olivier

AU - Mikkelsen, Kurt V.

AU - Juríček, Michal

AU - Nielsen, Mogens Brøndsted

N1 - Publisher Copyright: © 2022 The Authors. Energy Science & Engineering published by the Society of Chemical Industry and John Wiley & Sons Ltd.

PY - 2022

Y1 - 2022

N2 - Organic photovoltaics relies on the development of stable chromophores and redox-active organic molecules with tailor-made HOMO/LUMO energies. Here, we present the synthesis and properties of novel dyads composed of boron subphthalocyanine (SubPc) and triangulene units, connected either at the peripheral position of the subphthalocyanine or at the axial boron. The connectivity has strong implications for the absorption and fluorescence properties of the dyads, as well as their redox properties. While the SubPc unit has a bowl shape, triangulene is a planar structural unit that allows dyads to dimerize in the solid state on account of π-stacking interactions as shown by X-ray crystallography of one of the dyads. The electronic properties were also studied computationally by density functional theory methods. Excellent agreement between experimental and computed data were obtained, showing that our computational method is a strong tool in the rational design of optimum molecules to ultimately obtain finely tuned molecules for device applications.

AB - Organic photovoltaics relies on the development of stable chromophores and redox-active organic molecules with tailor-made HOMO/LUMO energies. Here, we present the synthesis and properties of novel dyads composed of boron subphthalocyanine (SubPc) and triangulene units, connected either at the peripheral position of the subphthalocyanine or at the axial boron. The connectivity has strong implications for the absorption and fluorescence properties of the dyads, as well as their redox properties. While the SubPc unit has a bowl shape, triangulene is a planar structural unit that allows dyads to dimerize in the solid state on account of π-stacking interactions as shown by X-ray crystallography of one of the dyads. The electronic properties were also studied computationally by density functional theory methods. Excellent agreement between experimental and computed data were obtained, showing that our computational method is a strong tool in the rational design of optimum molecules to ultimately obtain finely tuned molecules for device applications.

U2 - 10.1002/ese3.1071

DO - 10.1002/ese3.1071

M3 - Journal article

C2 - 35909459

AN - SCOPUS:85122782437

VL - 10

SP - 1752

EP - 1762

JO - Energy Science and Engineering

JF - Energy Science and Engineering

SN - 2050-0505

IS - 5

ER -