2H‐Dinaphthopentacene: A Polycyclic Aromatic Hydrocarbon Core for Metal‐Free Organic Sensitizers in Efficient Dye‐Sensitized Solar Cells

Abstract

Continuous studies on the use of a polycyclic aromatic hydrocarbon as the central block of an organic photosensitizer have brought forth a new opportunity toward efficiency enhancement of dye‐sensitized solar cells (DSCs). In this paper, a nonacyclic aromatic hydrocarbon 9,19‐dihydrodinaphtho[3,2,1‐de:3′,2′,1′‐op]pentacene, tethered with four 4‐hexylphenyl solubilizing groups is reported. The novel chromophore 9,9‐19‐19‐tetrakis(4‐hexylphenyl)‐9,19‐dihydrodinaphtho[3,2,1‐de:3′,2′,1′‐op]pentacene is further functionalized with diarylamines and 4‐(7‐ethynylbenzo[c][1,2,5]thiadiazol‐4‐yl)benzoic acid to produce two donor–acceptor (D–A) organic photosensitizers, achieving good power conversion efficiencies up to 10.2% in DSCs.

Evolution of the Excited‐State Dynamics of 2H‐Dinaphthopentacene Based Dyes in Dye‐Sensitized Solar Cells: From Chromophoric Core to Ultimate Dye

“…Materials : Toluene, chloroform, ethanol, acetonitrile, 4‐tert‐butylpyridine (TBP), and lithium bis(trifluoromentylsulfonyl)imide (LiTFSI) were obtained from Sigma–Aldrich. THPDNP, DPA‐THPDNP, DBPA‐THPDNP, R1, and R2 molecules were prepared according to preceding literature procedures …”

“…Rigidification of a molecular structure is a common method to elongate the lifetime of the excited‐state by abating non‐radiative deexcitation induced by torsional motion. In this regard, some rigid chromophore units, such as some polycyclic aromatic hydrocarbon (PAH) cores, N ‐annulated perylene, and 2 H ‐dinaphthopentacene, as well as their derivative segments characteristic of a coplanar skeleton have been exploited as building blocks for organic sensitizers, achieving considerable advancement in PCEs in recent years. Currently, the investigation of excited‐state dynamics is lagging behind the rapid development of these PAH‐based dyes, leading to an insufficient information basis for future design of advanced organic sensitizers.…”

Accelerated Discovery of Potential Organic Dyes for Dye‐Sensitized Solar Cells by Interpretable Machine Learning Models and Virtual Screening

“…Further improving the PCE of DSSCs requires design and synthesis of new high-efficiency organic dyes, which play a pivotal role in absorbing visible light and generating photocurrent. [9][10][11][12][13][14][15] However, the chemical space of possible organic dyes is extremely huge due to the vast number of functional groups and their various linkage combinations, and accordingly, the tedious and expensive trial-and-error experimental procedure becomes the bottleneck to find an optimal dye molecule from such a huge chemical space.…”

Molecular design of novel indacenodithiophene‐based organic dyes for efficient dye‐sensitized solar cells applications

“…Currently, most effective metal‐free organic dye sensitizers adopt a donor‐(π‐spacer)‐acceptor structure motif. For the donor part which provides electrons upon photoexcitation, coumarin, diphenylamine (DPA), triphenylamine (TPA), perylene, indoline, xanthene, squaraine, and other organic units have been commonly investigated for DSSC applications. While for the electron acceptor (A), the cyanoacrylic acid moiety or the 4‐(7‐ethynylbenzo[c][1,2,5]thiadiazol‐4‐yl) benzoic acid are two widely used electron acceptors for metal‐free organic dyes.…”