Synthesis and Search for Design Principles of New Electron Accepting Polymers for All-Polymer Solar Cells

N-Methylation has a significant impact on improving the oral bioavailability, lipophilicity and aqueous solubility of peptide-based lead drug structures. The selected mono-amino acid derivatives Ac-X-OMe, where X = Gly, Val, Leu, Ile, Phe, Met, Cys, Ser, Asp and His as well as their corresponding N-methylated analogues were studied. The clog P values of all N-methylated peptides are greater than those of native compounds. Quantum chemical calculations were performed to estimate the aqueous solubility of these lipophilic compounds using density functional theory (DFT). To confirm the contribution of dispersion forces on quantum chemical data, the long-range corrected (LC) hybrid density functional (ωB97X-D) was also probed for some amino acid derivatives. The ωB97X functional gave similar results. Our results reveal that after mono N-methylation of the peptide backbone, ΔGsolv becomes more negative (more water soluble) while polarizability and dipole moment are also increased. Natural atomic charges derived by natural bond orbital (NBO) analysis of N, C, and O atoms involved in amide functional group become more positive/(less negative) after N-methylation. All N-methylated amino acids have higher EHOMO (less negative) in comparison with the amino acid analogues, and in all cases N-methylation decreases EHOMO-LUMO. The calculated amide cis/trans activation energies (EA) of all the N-methylated amino acid derivatives were lower than that of native species. N-methylation of these compounds leads to an increase in lipophilicity, aqueous solubility, polarization, dipole moment and lowering of the cis/trans amide energy barrier (EA).

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“…[94,95] The latter is therefore also linked to solubility. [94,95] The latter is therefore also linked to solubility.…”

Section: Frontier Molecular Orbitals (Homo Lumo)mentioning

confidence: 99%

The effect of N-methylation of amino acids (Ac-X-OMe) on solubility and conformation: a DFT study

et al. 2015

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“…[14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29] Only in the last two years, larger PCEs (4-6%) have been reported. However, both systems normally show poor PCEs o3% or around 3%.…”

Section: Introductionmentioning

confidence: 99%

A perylene diimide (PDI)-based small molecule with tetrahedral configuration as a non-fullerene acceptor for organic solar cells

et al. 2015

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In this paper, a new perylene diimide (PDI)-based acceptor Me-PDI 4 with tetrahedral configuration (or 3D) has been synthesized and characterized. Solution-processed organic solar cells (OSCs) based on Me-PDI 4 have been investigated and our results show that the device performance can reach as high as 2.73%. Our new design with tetrahedral configuration (or 3D) could be an efficient approach to increase the PCE of OSCs with non-fullerene acceptors.

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“…Several criteria for designing electron accepting polymers for all-polymer solar cells were suggested. 26 It was suggested that accepting polymers should exhibit proper energy levels, internal 2 polarization and high electron mobility for high OPV performance.…”

Section: Introductionmentioning

confidence: 99%

Development and Structure/Property Relationship of New Electron Accepting Polymers Based on Thieno[2′,3′:4,5]pyrido[2,3-g]thieno[3,2-c]quinoline-4,10-dione for All-Polymer Solar Cells

et al. 2015

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Article Development and structure/property relationship of new electronaccepting polymers based on thieno[2',3':4,5]pyrido[2,3-g]thieno[3,2-c]quinoline-4,10-dione for all-polymer solar cells ABSTRACT: Several electron accepting polymers having weak accepting-strong accepting (WA-SA) and strong accepting-strong accepting (SA-SA) monomer alternation were synthesized for studies of structure/property relationship in all-polymer solar cells. Two kinds of cyclic amide monomers, 4,10-bis(2-butyloctyl)-thieno[2',3':5,6]pyrido[3,4-g]thieno-[3,2-c]isoquinoline-5,11-dione (TPTI) and 5,11-bis(2-butyloctyl)-thieno[2',3':4,5]pyrido[2,3-g]thieno[3,2-c]quinoline-4,10-dione (TPTQ) were synthesized as weak accepting monomers (WA). Difluorinated TPTQ (FTPTQ) and well-known perylene diimide (PDI) monomers were synthesized as strong electron accepting monomers (SA). By using 1-chloronaphthalene (CN) as a co-solvent, the morphology of the polymer blended films can be finely tuned to achieve better ordering toward face-on mode and favorable phase separation between electron donor and acceptor, resulting in significant enhancement of short circuit current (J sc ) and fill factor (FF). The fluorination in TPTQ unit reduced the dipole moment of D-A complex and gave a negative effect on a polymer system. PFP showed worse electron accepting property with lower electron mobility than PQP. It is reasoned that the internal polarization plays an important role in the design of electron accepting polymers. As a result, PQP having TPTQ monomer exhibited best photovoltaic performance with power conversion efficiency (PCE) of 3.52 % (V oc = 0.71 V, J sc = 8.57 mA/cm 2 , FF = 0.58) at a weight ratio of PTB7-Th:PQP = 1:1, under AM 1.5G.

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Synthesis and Search for Design Principles of New Electron Accepting Polymers for All-Polymer Solar Cells

Cited by 102 publications

References 59 publications

The effect of N-methylation of amino acids (Ac-X-OMe) on solubility and conformation: a DFT study

The effect of N-methylation of amino acids (Ac-X-OMe) on solubility and conformation: a DFT study

A perylene diimide (PDI)-based small molecule with tetrahedral configuration as a non-fullerene acceptor for organic solar cells

Development and Structure/Property Relationship of New Electron Accepting Polymers Based on Thieno[2′,3′:4,5]pyrido[2,3-g]thieno[3,2-c]quinoline-4,10-dione for All-Polymer Solar Cells

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