Ring-fusion as a perylenediimide dimer design concept for high-performance non-fullerene organic photovoltaic acceptors

Hartnett, Patrick E.; Matte, H. S. S. Ramakrishna; Eastham, Nicholas D.; Jackson, Nicholas E.; Wu, Yilei; Chen, Lin X.; Ratner, Mark A.; Chang, Robert P. H.; Hersam, Mark C.; Wasielewski, Michael R.; Marks, Tobin J.

doi:10.1039/c5sc04956c

Cited by 165 publications

(111 citation statements)

References 84 publications

(80 reference statements)

Supporting

Mentioning

105

Contrasting

Order By: Relevance

“…Intramolecular oxidative coupling has also been used as ac onvenient procedure for the ring fusion of perylene diimides (PDI), [172][173][174] as well as for p-expansions of BODIPY and aza-BODIPY-based dyes, [175][176][177][178][179] which has led to significant bathochromic shifts of the absorption and emission maxima. Al ibrary of p-expanded imidazoles has been prepared by employing aPIFA/BF 3 ·Et 2 Osystem for the oxidative cyclization of variously substituted 1,2,4,5-tetraarylimidazole derivatives.…”

Section: Dyes and Heterocyclic Polyarenesmentioning

confidence: 99%

Synthetic Applications of Oxidative Aromatic Coupling—From Biphenols to Nanographenes

et al. 2019

View full text Add to dashboard Cite

Oxidative aromatic coupling occupies a fundamental place in the modern chemistry of aromatic compounds. It is a method of choice for the assembly of large and bewildering architectures. Considerable effort was also devoted to applications of the Scholl reaction for the synthesis of chiral biphenols and natural products. The ability to form biaryl linkages without any prefunctionalization provides an efficient pathway to many complex structures. Although the chemistry of this process is only now becoming fully understood, this reaction continues to both fascinate and challenge researchers. This is especially true for heterocoupling, that is, oxidative aromatic coupling with the chemoselective formation of a C−C bond between two different arenes. Analysis of the progress achieved in this field since 2013 reveals that many groups have contributed by pushing the boundary of structural possibilities, expanding into surface‐assisted (cyclo)dehydrogenation, and developing new reagents.

show abstract

Section: Dyes and Heterocyclic Polyarenesmentioning

confidence: 99%

Synthetic Applications of Oxidative Aromatic Coupling—From Biphenols to Nanographenes

et al. 2019

View full text Add to dashboard Cite

show abstract

“…[80] In the past 10 years,the Katz-modified Mallory reaction has been used to prepare aw ide variety of PA Hs,t he most popular examples being coronenes [81][82][83][84][85] and fused perylenediimides (PDIs). [86][87][88][89][90][91][92][93][94][95] Despite the success of this reaction to prepare nanographenes in high yields,t here are rare examples of its use for the synthesis of GNRs.Nuckolls and co-workers were the first to report the use of the Mallory reaction for the synthesis of finite-length GNRs.Starting from monobromo,dibromo and monostannane derivatives (21-23,S cheme 5), the PDI units were linked together through aS tille coupling using an iterative approach and the rigid ribbon structures were formed by aM allory reaction (compounds [24][25][26]. [96] Theoretical calculations suggest that these ribbons adopt ac onformation that is either waggling or helical.…”

Section: Mallory Reactionmentioning

confidence: 99%

Section: Mallory Reactionmentioning

confidence: 99%

Emerging Bottom‐Up Strategies for the Synthesis of Graphene Nanoribbons and Related Structures

et al. 2019

View full text Add to dashboard Cite

The solution‐phase synthesis is one of the most promising strategies for the preparation of well‐defined graphene nanoribbons (GNRs) in large scale. To prepare high quality, defect‐free GNRs, cycloaromatization reactions need to be very efficient, proceed without side reaction and mild enough to accommodate the presence of various functional groups. In this Minireview, we present the latest synthetic approaches for the synthesis of GNRs and related structures, including alkyne benzannulation, photochemical cyclodehydrohalogenation, Mallory and Pd‐ and Ni‐catalyzed reactions.

show abstract

“…The n -type semiconductors used as acceptor in the PSCs include fullerene derivatives4, n -type conjugated polymers56789101112 and n -type organic semiconductors ( n -OS)1314151617181920212223. Among the acceptors, n -OS acceptors show distinguished advantages of easy tuning of absorption and electronic energy levels, strong absorbance, good morphology stability and more suitable for flexible devices.…”

mentioning

confidence: 99%

11.4% Efficiency non-fullerene polymer solar cells with trialkylsilyl substituted 2D-conjugated polymer as donor

et al. 2016

View full text Add to dashboard Cite

Simutaneously high open circuit voltage and high short circuit current density is a big challenge for achieving high efficiency polymer solar cells due to the excitonic nature of organic semdonductors. Herein, we developed a trialkylsilyl substituted 2D-conjugated polymer with the highest occupied molecular orbital level down-shifted by Si–C bond interaction. The polymer solar cells obtained by pairing this polymer with a non-fullerene acceptor demonstrated a high power conversion efficiency of 11.41% with both high open circuit voltage of 0.94 V and high short circuit current density of 17.32 mA cm−2 benefitted from the complementary absorption of the donor and acceptor, and the high hole transfer efficiency from acceptor to donor although the highest occupied molecular orbital level difference between the donor and acceptor is only 0.11 eV. The results indicate that the alkylsilyl substitution is an effective way in designing high performance conjugated polymer photovoltaic materials.

show abstract

Ring-fusion as a perylenediimide dimer design concept for high-performance non-fullerene organic photovoltaic acceptors

Abstract: A series of perylenediimide (PDI) dimers are evaluated as acceptors for organic photovoltaic (OPV) cells.

Cited by 165 publications

References 84 publications

Synthetic Applications of Oxidative Aromatic Coupling—From Biphenols to Nanographenes

Synthetic Applications of Oxidative Aromatic Coupling—From Biphenols to Nanographenes

Emerging Bottom‐Up Strategies for the Synthesis of Graphene Nanoribbons and Related Structures

11.4% Efficiency non-fullerene polymer solar cells with trialkylsilyl substituted 2D-conjugated polymer as donor

Contact Info

Product

Resources

About