A ring fused N-annulated PDI non-fullerene acceptor for high open circuit voltage solar cells processed from non-halogenated solvents

Laventure, Audrey; Stanzel, Samantha; Payne, Abby‐Jo; Lessard, Benoît H.; Welch, Gregory C.

doi:10.1016/j.synthmet.2019.02.010

Cited by 23 publications

(20 citation statements)

References 55 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…PDI is a promising unit to design new NFAs, particularly because of its low cost, strong molar absorption in the visible range, tunable optoelectronic properties and good charge transport. [96][97][98][99][100] TPDI2N-EH (Figure 5) showed a wide optical bandgap of 2.22 eV, leading to photoabsorption between 400 and conditions previously mentioned, TPDI2N-EH:PPDT2FBT blend achieved a VOC of 0.84V, representing a small ΔV of 0.18V. Consequently, the PCE increased by more than 2 fold under ambient conditions, to reach a value of 9.6%.…”

Section: Acceptor Materials For Iopvsmentioning

confidence: 72%

Recent Progress on Indoor Organic Photovoltaics: From Molecular Design to Production Scale

2020

View full text Add to dashboard Cite

Recently, indoor photovoltaics have attracted much interest for their ability to power small electronic devices and sensors, especially with the growth of the Internet of Things (IoT). Due to their absorption covering ambient emission spectra and tunable electronic structures, π-conjugated polymers and small molecules are well-suited for these applications. Among many benefits, including their ink processability, lightweight and flexibility; indoor organic photovoltaics (IOPVs) show power conversion efficiencies (PCE) over 26%. It represents a power output over 30 μW cm -2 under office light (500 lux), which is sufficient to operate many electronic devices and sensors with a relatively small photovoltaic area. This focus review highlights the major advances in the material design for IOPVs and includes some industrial insights to reach the production scale criteria.''Internet of Things'' over the last decades. Data were taken from Web of Science database on January 6 th , 2020.

show abstract

Section: Acceptor Materials For Iopvsmentioning

confidence: 72%

Recent Progress on Indoor Organic Photovoltaics: From Molecular Design to Production Scale

2020

View full text Add to dashboard Cite

show abstract

“…Materials PTB7-Th (130 kg mol −1 ) was purchased from 1-Material (Montréal, QC, Canada). NPDI 2 , 27 T-NPDI 2 , 38 F-NPDI 2, 39 and NPDI 4 32 were synthesized as previously reported.…”

Section: Methodsmentioning

confidence: 99%

“…Three of these compounds were dimers without or with a core: no π-core unit (NPDI 2 ), 27 a thiophene unit (T-NPDI 2 ) 38 (unfused) and its counterpart with a fused thiophene unit (F-NPDI 2 ). 39 The fourth was a tetramer (NPDI 4 ), with a ladder-type core (indacenodithiophene, IDT). 32 The NPDI x compounds have a high optical absorption coefficient (>100 000 L mol −1 cm −1 for the dimers and >200 000 L mol −1 cm −1 for the tetramer) in the 400-600 nm range, typical of PDI-based materials.…”

Section: Selection Of Materialsmentioning

confidence: 99%

N‐Annulated perylene diimide dimers and tetramer non‐fullerene acceptors: impact of solvent processing additive on their thin film formation behavior

Laventure

Stanzel

Payne

et al. 2021

J of Chemical Tech & Biotech

Self Cite

View full text Add to dashboard Cite

BACKGROUND: We aim to determine whether the rationale of designing a tetrameric non-fullerene acceptor (NFA) to minimize its aggregation compared to its dimer counterparts proves to be a valid strategy in the context of organic photovoltaic (OPV) processing involving solvent additives. We investigate the impact of the molecular design and the processing additive on the thin film formation behavior of four N-annulated perylene diimide (NPDI x ) derivatives. We compare three dimers and a tetramer, processed from a solution containing 1,8-diiodooctane (DIO), which are used as NFAs and as a processing solvent additive, respectively, in the OPV fabrication.RESULTS: We prepared OPV devices using the PTB7-Th:NPDI x model system and rationalized the change in their power conversion efficiency (PCE) based on the thin film morphology of the four NDPI x compounds. While the PCE of the OPV devices prepared using the dimers and 1% (v/v) DIO showed a 20-30% drop, those prepared using the tetramer and the same processing conditions showed an 80% drop. Our analysis demonstrates that DIO processing solvent additive-induced crystallization of the tetramer is the cause of its low performance in OPV devices. CONCLUSION: Our results highlight that relying solely on the tetramer perylene diimide design strategy to prevent the aggregation observed in dimers is not always reliable when processing solvent additives are used in the OPV fabrication. Both the molecular design and the processing solvent additive impact the aggregation behavior of the NFA and need to be taken into account to optimize OPV devices active layer morphology.

show abstract

“…Since DPTs have proven promise in optoelectronic applications, [4,5,23,58,59] the optical and electrochemical characteristics of a new set of PTs and DPTs were examined along with synthetically important novel aza-analogue 17 and the carboanalogue tetrabenzospirobifluorene 18 (for complete details, see Figures S56-S104 and Tables S1-S3). Key results of some selected DPTs (6 b, 8-9, 10 b, 11, 13 b, 14 c, 17 and 18) are summarized in Table 1.…”

Section: Optical and Electrochemical Propertiesmentioning

confidence: 99%

Steering Scholl Oxidative Heterocoupling by Tuning Topology and Electronics for Building Thiananographenes and Their Functional N−/C−Congeners

Maddala

Panua

Venkatakrishnan

2021

Chemistry A European J

View full text Add to dashboard Cite

While intramolecular Scholl oxidative coupling between two arenes is common, successful CÀ C heterocoupling between thiophene and arene is scarce. The latter is due to the notorious reactivity of thiophene towards polymerization under oxidative conditions. This report systematically demonstrates how topological variation of electronics and reactivity in thiophene substrates can lead to efficient oxidative heterocoupling. Bis(biaryl)thiophenes having reactive αand β-positions open are the choice of substrates. The cyclizing arene partners are so electronically tuned for thiophene's reactivity (at αand β-) as to establish CÀ C bond oxidatively generating symmetrical as well as unsymmetrical diphenanthrothiophenes which are basic thiananographenes. Depending on the cyclizing-couple's electronics, either areneor thiophene-centered oxidation initiates CÀ C heterocoupling. The potential utility of these simple thiananographenes is further unfurled by converting them to functional NÀ /Cgraphene segments that are aza-corannulene precursor and tetrabenzospirobifluorene. Their bright emission and extended electrochemical stability are remarkable that may be potentially important and applicable.

show abstract

A ring fused N-annulated PDI non-fullerene acceptor for high open circuit voltage solar cells processed from non-halogenated solvents

Cited by 23 publications

References 55 publications

Recent Progress on Indoor Organic Photovoltaics: From Molecular Design to Production Scale

Recent Progress on Indoor Organic Photovoltaics: From Molecular Design to Production Scale

N‐Annulated perylene diimide dimers and tetramer non‐fullerene acceptors: impact of solvent processing additive on their thin film formation behavior

Steering Scholl Oxidative Heterocoupling by Tuning Topology and Electronics for Building Thiananographenes and Their Functional N−/C−Congeners

Contact Info

Product

Resources

About