Consequences of hydrogen bonding on molecular organization and charge transport in molecular organic photovoltaic materials

Schulze, Benjamin M.; Shewmon, Nathan T.; Zhang, Jing; Watkins, Davita L.; Mudrick, John; Cao, Weiran; Zerdan, Raghida Bou; Quartararo, Anthony J.; Ghiviriga, Ion; Xue, Jiangeng; Castellano, Ronald K.

doi:10.1039/c3ta13529b

Cited by 39 publications

(54 citation statements)

References 71 publications

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“…S4). While slightly different arrangements may be anticipated for three-dimensional C 60 /MeBQPH assemblies in the donor/acceptor BHJ (vs. the bilayer structure studied here), the present results suggest that the C 60 molecules would not hinder the ability of the MeBQPH trimer rosettes to stack through p-p interactions in the direction normal to the substrate, a promising first step towards forming the vertically aligned donor trimer domains as previously anticipated [17]. Unfortunately, we were not successful in imaging these organic films beyond one or two monolayers under STM, likely due to a combination of the relatively low electrical conductivity of these organic semiconductors and weak adhesion between molecular layers.…”

Section: Assembly On a Mebqph Monolayersupporting

confidence: 42%

“…MeBQPH and MeBQPME were prepared according to a previously published procedure [17]. The Au(1 1 1) substrate was prepared by annealing Au films on mica with a hydrogen-oxygen flame ex-situ.…”

Section: Sample Preparationmentioning

confidence: 99%

“…1d) in solution, a result consistent with earlier work [27,28], and to persist in both neat films and films blended with C 60 . We hypothesized that p-stacking between the H-bonded trimers could lead to vertically aligned, columnar donor domains with the C 60 acceptor molecules occupying the void space in between donor columns, thus forming a stable BHJ morphology that facilitates charge generation and transport [17]. Despite compelling device parameter improvements, challenges remain to definitively link them to an underlying supramolecular structure that is dictated by H-bonding and to realize a molecular level understanding of H-bonded donor assembly and possible donor-acceptor interface structures.…”

Section: Introductionmentioning

confidence: 99%

“…We [17], and others [18][19][20][21][22][23][24][25][26], are attempting to use directed hydrogen bonding (H-bonding) interactions to rationally control the assembly of molecular electron donors in BHJ OPVs. Our specific goal is to allow tailored self-complementary H-bonding between p-conjugated oligomers to work synergistically with p-stacking to improve the nanoscale morphology of donor-C 60 blends [17].…”

Section: Introductionmentioning

confidence: 99%

“…Our specific goal is to allow tailored self-complementary H-bonding between p-conjugated oligomers to work synergistically with p-stacking to improve the nanoscale morphology of donor-C 60 blends [17]. A phthalhydrazide (PH) functionalized branched quaterthiophene (BQ) derivative, MeBQPH ( Fig.…”

Section: Introductionmentioning

confidence: 99%

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Hydrogen bond directed assembly of oligothiophene/fullerene superstructures on Au(111)

Zhao

Watkins

Galindo

et al. 2015

Organic Electronics

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Section: Assembly On a Mebqph Monolayersupporting

confidence: 42%

Section: Sample Preparationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Hydrogen bond directed assembly of oligothiophene/fullerene superstructures on Au(111)

Zhao

Watkins

Galindo

et al. 2015

Organic Electronics

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Enhancement in Organic Photovoltaic Efficiency through the Synergistic Interplay of Molecular Donor Hydrogen Bonding and π‐Stacking

Shewmon

Watkins

Galindo

et al. 2015

Adv Funct Materials

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For organic photovoltaic (OPV) cells based on the bulk heterojunction (BHJ) structure, it remains challenging to rationally control the degree of phase separation and percolation within blends of donors and acceptors to secure optimal charge separation and transport. Reported is a bottom‐up, supramolecular approach to BHJ OPVs wherein tailored hydrogen bonding (H‐bonding) interactions between π‐conjugated electron donor molecules encourage formation of vertically aligned donor π‐stacks while simultaneously suppressing lateral aggregation; the programmed arrangement facilitates fine mixing with fullerene acceptors and efficient charge transport. The approach is illustrated using conventional linear or branched quaterthiophene donor chromophores outfitted with terminal functional groups that are either capable or incapable of self‐complementary H‐bonding. When applied to OPVs, the H‐bond capable donors yield a twofold enhancement in power conversion efficiency relative to the comparator systems, with a maximum external quantum efficiency of 64%. H‐bond promoted assembly results in redshifted absorption (in neat films and donor:C60 blends) and enhanced charge collection efficiency despite disparate donor chromophore structure. Both features positively impact photocurrent and fill factor in OPV devices. Film structural characterization by atomic force microscopy, transmission electron microscopy, and grazing incidence wide angle X‐ray scattering reveals a synergistic interplay of lateral H‐bonding interactions and vertical π‐stacking for directing the favorable morphology of the BHJ.

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Hydrogen Bond Induced Green Solvent Processed High Performance Ternary Organic Solar Cells with Good Tolerance on Film Thickness and Blend Ratios

Zhao

et al. 2019

Adv Funct Materials

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For comprehensive development of organic solar cells (OSCs), some factors such as environmental stability, low cost, insensitive film thickness, component contents tolerance, and green preparation processes are equally crucial to achieve high power conversion efficiencies (PCEs). In this work, a small molecule 3-(diethylamino)-7-imino-7H-benzo[4,5]imidazo[1,2-a]chromeno[3,2-c]pyridine-6-carbonitrile (DIBC), which is commercially available at low cost, is utilized to realize high-performance ternary OSCs. Demonstrated via Fourier transform infrared and 2D-1 HNMR, DIBC can form hydrogen bond interactions with [6,6]-phenyl-C 71 -butyric acid methyl ester (PC 71 BM) in solid films. Further electrostatic potential (ESP) calculations indicate that the hydrogen bond interaction enhances the ESP of PC 71 BM and accelerates charge transport between donor and acceptor. As a result, poly(4,8-bis(5-(2-ethylhexyl)thiophen-2-yl) benzo[1,2-b;4,5-b0]dithiophene-2,6diylalt-(4-(2-ethylhexyl)-3-fluorothieno[3,4-b]thiophene-)-2-carboxylate-2-6-diyl(PTB7-Th):DIBC:PC 71 BM-based ternary OSC achieves a maximum efficiency of 12.17%, which is the best result of green solvent processed fullerene OSCs at present. It is noteworthy that the ternary OSCs also show great tolerance to film thickness and blend ratios. These unique properties are attributed to the hydrogen-bond-linked DIBC and PC 71 BM, which modulates molecule distribution and improves film morphology with an interpenetrating network structure. Furthermore, the DIBC containing device also exhibits good thermal and light radiation stability. These results illustrate that intermolecular hydrogen bond interaction has great potential for realizing high-performance OSCs.

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Consequences of hydrogen bonding on molecular organization and charge transport in molecular organic photovoltaic materials

Cited by 39 publications

References 71 publications

Hydrogen bond directed assembly of oligothiophene/fullerene superstructures on Au(111)

Hydrogen bond directed assembly of oligothiophene/fullerene superstructures on Au(111)

Enhancement in Organic Photovoltaic Efficiency through the Synergistic Interplay of Molecular Donor Hydrogen Bonding and π‐Stacking

Hydrogen Bond Induced Green Solvent Processed High Performance Ternary Organic Solar Cells with Good Tolerance on Film Thickness and Blend Ratios

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