Organic Donor–Acceptor Assemblies form Coaxial p–n Heterojunctions with High Photoconductivity

Prasanthkumar, Seelam; Ghosh, Samrat; Vijayakumar, Chakkooth; Saeki, Akinori; Seki, Shu; Ajayaghosh, Ayyappanpillai

doi:10.1002/anie.201408831

Cited by 137 publications

(118 citation statements)

References 83 publications

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“…12,13 But also due to the strong p-p self-stacking, PTCDI molecules intend to form homogeneous assembly of themselves, even in the presence of electron donor molecules. [14][15][16][17][18][19] To form D-A cocrystals, the molecular structure must be designed so that the D-A interaction exceeds the p-p stacking between PTCDIs, while still maintains the overall geometry matching for the cofacial intermolecular arrangement for a crystalline phase. Because of this structural design challenge, few D-A cocrystal structures of PTCDI was reported, 5 and the high quality cocrystals are thereby highly desired.…”

Section: 2mentioning

confidence: 99%

Donor–acceptor single cocrystal of coronene and perylene diimide: molecular self-assembly and charge-transfer photoluminescence

Wang

et al. 2017

RSC Adv.

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The research on donor-acceptor (D-A) cocrystalline structures based on organic semiconductive molecules has drawn great attention due to their unique optical and electronic properties. Among the building block molecules, derivatives of perylene-3,4,9,10-tetracarboxylic-3,4,9,10-diimides (PTCDI) are of particular interest as these molecules form high performance n-type semiconductors with strong air stability. However, the cocrystal of PTCDIs remains challenging to fabricate, and only few D-A cocrystals of PTCDIs have been reported. Herein, we report a successful molecular self-assembly design for the PTCDI cocrystal with a donor molecule, coronene. Within the triclinic cell of the cocrystal, the PTCDI and coronene molecules achieved 1 : 1 alternated p-p stacking. The cocrystal showed clear red-shifted absorption and photoluminescence bands, implying the strong charge transfer interaction between coronene and PTCDI. Additionally, the cofacial p-p stacking between coronene and PTCDI planes favors strong one-dimensional self-assembly, leading to the formation of microsized fibril cocrystals and arrays. This presented cocrystal design strategy helps to explore new D-A cocrystalline structures, particularly with one-dimensional morphology control.

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Section: 2mentioning

confidence: 99%

Donor–acceptor single cocrystal of coronene and perylene diimide: molecular self-assembly and charge-transfer photoluminescence

Wang

et al. 2017

RSC Adv.

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“…The dramatic improvement in charge carrier mobility in case of SMBC1 compared to pure PBI is owing to more ordered arrangement of the PBI molecules inside the block copolymer domain with stronger π–π stacking and shorter stacking distance facilitating intermolecular electronic communication compared to pure PBI. There are several reports of such enhancement in charge carrier mobility of organic semiconductor system due to self‐assembly . The different aggregation of PBI molecules in SMBCs compared to pure PBI is also proved from optical, luminescence, and X‐ray diffraction (XRD) study.…”

Section: Resultsmentioning

confidence: 88%

Enhanced Charge Carrier Mobility and Tailored Luminescence of n‐Type Organic Semiconductor through Block Copolymer Supramolecular Assembly

Kumari

Khawas

Bera

et al. 2017

Macro Chemistry & Physics

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Herein, a novel and viable strategy to fabricate fully solution processable nanostructured n‐type organic semiconducting material through block copolymer supramolecular assembly consisting of polystyrene‐b‐poly(4‐vinyl pyridine) (PS‐b‐P4VP) and an asymmetric perylenebisimide (PBI) has been demonstrated. The block copolymer supramolecular assemblies show hierarchical structure formation in two length scales (lamella within lamella) from synergistic phase separation of block copolymer and PBI molecule inside the comb block. The optical and luminescent studies clearly evidence that the nature of aggregation of the PBI molecules inside the P4VP domain through facial π–π stacking is modified with tailored luminescent properties compared to its pure state. The block copolymer supramolecular assembly with 1:1 mole ratio (4‐vinyl pyridine:PBI) shows almost three‐order enhancement of charge carrier mobility compared to pristine PBI though it has only (0.571) of PBI weight fraction. It is believed that the organic semiconductor polymeric system described here will be useful for preparing luminescent materials, organic electronic and optoelectronic devices.

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“…Ajayaghosh and coworkers reported the self‐sorting of structurally dissimilar p‐type and n‐type semiconductorS based on trithienylenevinylene (TTV; 34) and perylene diimide (PDI; 33) derivatives, respectively (Figure ) . The mixture of TTV/PDI (1 : 1) in n‐decane, didn't show any CT‐band owing to the difference in strength of non‐covalent interactions.…”

Section: Discussionmentioning

confidence: 99%

Self‐Sorting in Supramolecular Assembly of π‐Systems

Kar

Ghosh

2019

Israel Journal of Chemistry

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Self‐sorting is a term, which broadly identifies sorting out the individual components within a mixture, which is ubiquitous in Nature. In the recent past such self‐sorting phenomenon has been studied with great interest in supramolecular assembly of wide‐ranging building blocks. In this article, we particularly highlight the examples related to self‐sorting in co‐assembly of donor and acceptor type chromophoric systems. Supramolecular design principles based on immiscibility of chromophore appended chains, π‐surface mismatch, H‐bonding, chirality and others have been discussed in length. Examples correlating molecular assembly features with macroscopic picture have also been discussed particularly in context of implications in organic electronic applications of self‐sorted donor acceptor assemblies.

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Organic Donor–Acceptor Assemblies form Coaxial p–n Heterojunctions with High Photoconductivity

Cited by 137 publications

References 83 publications

Donor–acceptor single cocrystal of coronene and perylene diimide: molecular self-assembly and charge-transfer photoluminescence

Donor–acceptor single cocrystal of coronene and perylene diimide: molecular self-assembly and charge-transfer photoluminescence

Enhanced Charge Carrier Mobility and Tailored Luminescence of n‐Type Organic Semiconductor through Block Copolymer Supramolecular Assembly

Self‐Sorting in Supramolecular Assembly of π‐Systems

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