Small molecules containing rigidified thiophenes and a cyanopyridone acceptor unit for solution-processable bulk-heterojunction solar cells

Gupta, Akhil; Ali, Abdelselam; Gao, Mei; Singh, Th. Birendra; Bilić, Ante; Watkins, Scott E.; Bach, Udo; Evans, Richard A.

doi:10.1016/j.dyepig.2015.03.028

Cited by 21 publications

(11 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A, Training set: from yellow to blue, according to the experimental PCE (yellow, low; blue, high PCE); test set: red squares. B, Training set: gray; test set color‐scale according to scaffold similarity: compounds from Brabec et al (purple), compounds from Cheng et al (yellow), compounds from Sun et al (violet), compounds from Montcada et al (green), compounds from Löbert et al (pale blue), compounds from Montcada et al (pink), compounds from Gupta et al (orange)…”

Section: Resultsmentioning

confidence: 99%

Quantitative structure‐property relationship modeling of small organic molecules for solar cells applications

Tortorella

Angelis

Cruciani

2017

Journal of Chemometrics

View full text Add to dashboard Cite

Despite the need of a reliable technology for solar energy harvesting, research on new materials for third generation photovoltaics is slowed down by the diffuse use of trial and error rather than rational material design approaches. The proposed study investigates the use of alternative strategies to material discovery inspired by drug design and molecular modeling. In particular, training set and test set (for validation purposes) comprising well‐known small molecule‐bulk heterojunction organic photovoltaics were built. Molecules were characterized by semiempirical calculated and 3D molecular interaction fields–based descriptors. Then partial least squares algorithm was applied to rationalize structure‐photovoltaic activity relationships, and coefficients were investigated to clarify contributions played by the different molecular properties to the final performance. In addition, a photovoltaic desirability function (PhotD) was also proposed as alternative and versatile novel tool for ranking potential candidates. The partial least squares model and PhotD function were both internally and externally validated demonstrating their ability in estimating new candidates performances. The proposed approach demonstrates that, in the context of computational materials science, chemometrics and molecular modeling tools could effectively boost the discovery of novel promising candidates for photovoltaic application.

show abstract

Section: Resultsmentioning

confidence: 99%

Quantitative structure‐property relationship modeling of small organic molecules for solar cells applications

Tortorella

Angelis

Cruciani

2017

Journal of Chemometrics

View full text Add to dashboard Cite

show abstract

“…Samples for PESA were prepared on clean glass substrates. Fabrication and characterization of BHJ devices, and preparation of thin-film transistors has been reported previously [18,30].…”

Section: Methodsmentioning

confidence: 99%

“…Recent years have seen a dramatic surge not only in terms of device efficiency using small molecular donors but also in their design and efficient synthetic development. A variety of small molecule donor materials based on donor–acceptor (D–A) combinations such as D–A–D [25,26,27], A–D–A [28,29], D–π–A [18,19,30] and star-shaped architectures [31] have been reported. The D–A–D design in particular is one of the most promising and successful modules based on which various donor and acceptor units have been explored for high-performance solution-processable photovoltaic devices.…”

Section: Introductionmentioning

confidence: 99%

Significant Improvement of Optoelectronic and Photovoltaic Properties by Incorporating Thiophene in a Solution-Processable D–A–D Modular Chromophore

et al. 2015

Self Cite

View full text Add to dashboard Cite

Through the incorporation of a thiophene functionality, a novel solution-processable small organic chromophore was designed, synthesized and characterized for application in bulk-heterojunction solar cells. The new chromophore, (2Z,2 1 Z)-2,2 1 -(1,4-phenylene)bis(3-(5-(4-(diphenylamino)phenyl)thiophen-2-yl)acrylonitrile) (coded as AS2), was based on a donoracceptor-donor (D-A-D) module where a simple triphenylamine unit served as an electron donor, 1,4-phenylenediacetonitrile as an electron acceptor, and a thiophene ring as the π-bridge embedded between the donor and acceptor functionalities. AS2 was isolated as brick-red, needle-shaped crystals, and was fully characterized by 1 H-and 13 C-NMR, IR, mass spectrometry and single crystal X-ray diffraction. The optoelectronic and photovoltaic properties of AS2 were compared with those of a structural analogue, (2Z,2 1 Z)-2,2 1 -(1,4-phenylene)bis(3-(4-(diphenylamino)phenyl)-acrylonitrile) (AS1). Benefiting from the covalent thiophene bridges, compared to AS1 thin solid film, the AS2 film showed: (1) an enhancement of light-harvesting ability by 20%; (2) an increase in wavelength of the longest wavelength absorption maximum (497 nm vs. 470 nm) and (3) a narrower optical band-gap (1.93 eV vs. 2.17 eV). Studies on the photovoltaic properties revealed that the best AS2-[6,6]-phenyl-C 61 -butyric acid methyl ester (PC 61 BM)-based device showed an impressive enhanced power conversion efficiency of 4.10%, an approx. 3-fold increase with respect to the efficiency of the best AS1-based device (1.23%). These results clearly indicated that embodiment of thiophene functionality extended the molecular conjugation, thus enhancing the light-harvesting ability and short-circuit current density, while further improving the bulk-heterojunction device performance. To our knowledge, AS2 is the first example in the literature where a thiophene unit has been used in conjunction with a 1,4-phenylenediacetonitrile accepting functionality to extend the π-conjugation in a given D-A-D motif for bulk-heterojunction solar cell applications.

show abstract

“…Bithiophene‐based materials have been at the research forefront for their remarkable characteristics namely low oxidation potential, low energy gaps, and high thermal stability [17–23] . The electronic rich property of thiophene rings is known to provide a good number of electrons for the whole system.…”

Section: Introductionmentioning

confidence: 99%

“…Bithiophene-based materials have been at the research forefront for their remarkable characteristics namely low oxidation potential, low energy gaps, and high thermal stability. [17][18][19][20][21][22][23] The electronic rich property of thiophene rings is known to provide a good number of electrons for the whole system. On contrary, five-membered heterocycle imidazole possesses two distinct nitrogen atoms N1 and N3 being electron rich like pyrrole and electron-deficient like pyridine respectively.…”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of New Bithiophene Based Planar AIE Red Light Emitters: A Detailed Theoretical and Experimental Analysis**

2022

View full text Add to dashboard Cite

Bithiophene core with −CN substituted pyrazole and imidazole side chains yielding B1, B2, and B3 have been designed and synthesized viz Schiff's base condensation reaction. Molecules, at their solid‐state exhibited red‐light emission supporting AIE mechanism. The series exhibited the highest relative quantum yield of value 18.66 % by B1 with the lowest recorded for B3 exhibiting 2.4 %. DFT results reveal the synthesized molecules at their optimized ground state adopt a planar structure. Theoretical calculation further validates the molecules to adopt a slip‐stacking type of molecular packing arrangement at its condensed state, conducive for AIE. A large π‐π stacking distance between the lattice plane of 3.4 Å, 3.6 Å and 3.5 Å possessed by B1, B2, and B3 respectively, favors AIE. Computational calculation on electron and hole reorganization energy reveals the effective role of two −CN groups in altering the hole mobility in comparison with the other molecules in the series.

show abstract

Small molecules containing rigidified thiophenes and a cyanopyridone acceptor unit for solution-processable bulk-heterojunction solar cells

Cited by 21 publications

References 38 publications

Quantitative structure‐property relationship modeling of small organic molecules for solar cells applications

Quantitative structure‐property relationship modeling of small organic molecules for solar cells applications

Significant Improvement of Optoelectronic and Photovoltaic Properties by Incorporating Thiophene in a Solution-Processable D–A–D Modular Chromophore

Design and Synthesis of New Bithiophene Based Planar AIE Red Light Emitters: A Detailed Theoretical and Experimental Analysis**

Contact Info

Product

Resources

About