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07 Jan 11:47

Recent Progress in Printable Organic Field Effect Transistors

J. Mater. Chem. C, 2018, Accepted Manuscript
DOI: 10.1039/C8TC05485A, Review Article
Wei Tang, Yukun Huang, Lei Han, Ruili Liu, Yuezeng Su, Xiaojun Guo, Feng Yan
Printable organic field effect transistors (OFETs) have been investigated for more than 20 years, aiming at various emerging applications including flexible/wearable electronics, displays and sensors. Since many comprehensive review articles...
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23 Dec 08:23

Competition between Exceptionally Long‐Range Alkyl Sidechain Ordering and Backbone Ordering in Semiconducting Polymers and Its Impact on Electronic and Optoelectronic Properties

by Joshua H. Carpenter, Masoud Ghasemi, Eliot Gann, Indunil Angunawela, Samuel J. Stuard, Jeromy James Rech, Earl Ritchie, Brendan T. O'Connor, Joanna Atkin, Wei You, Dean M. DeLongchamp, Harald Ade
Advanced Functional Materials Competition between Exceptionally Long‐Range Alkyl Sidechain Ordering and Backbone Ordering in Semiconducting Polymers and Its Impact on Electronic and Optoelectronic Properties

A crystalline alkyl sidechain phase with coherence lengths >70 nm is reported in a series of representative semiconducting polymers. This ordering induces backbone disorder, revealing competing forces of the backbone and sidechain that prevent simultaneous ordering of both the constituents. Implications for molecular design that facilitates synergistic long‐range crystallization are discussed.


Abstract

Intra‐ and intermolecular ordering greatly impacts the electronic and optoelectronic properties of semiconducting polymers. The interrelationship between ordering of alkyl sidechains and conjugated backbones has yet to be fully detailed, despite much prior effort. Here, the discovery of a highly ordered alkyl sidechain phase in six representative semiconducting polymers, determined from distinct spectroscopic and diffraction signatures, is reported. The sidechain ordering exhibits unusually large coherence lengths (≥70 nm), induces torsional/twisting backbone disorder, and results in a vertically multilayered nanostructure with ordered sidechain layers alternating with disordered backbone layers. Calorimetry and in situ variable temperature scattering measurements in a model system poly{4‐(5‐(4,8‐bis(3‐butylnonyl)‐6‐methylbenzo[1,2‐b:4,5‐b′]dithiophen‐2‐yl)thiophen‐2‐yl)‐2‐(2‐butyloctyl)‐5,6‐difluoro‐7‐(5‐methylthiophen‐2‐yl)‐2H‐benzo[d][1,2,3]triazole} (PBnDT‐FTAZ) clearly delineate this competition of ordering that prevents simultaneous long‐range order of both moieties. The long‐range sidechain ordering can be exploited as a transient state to fabricate PBnDT‐FTAZ films with an atypical edge‐on texture and 2.5× improved field‐effect transistor mobility. The observed influence of ordering between the moieties implies that improved molecular design can produce synergistic rather than destructive ordering effects. Given the large sidechain coherence lengths observed, such synergistic ordering should greatly improve the coherence length of backbone ordering and thereby improve electronic and optoelectronic properties such as charge transport and exciton diffusion lengths.

17 Nov 10:29

Pyrene-fused PDI based ternary solar cells: high power conversion efficiency over 10%, and improved device thermal stability

Mater. Chem. Front., 2019, 3,93-102
DOI: 10.1039/C8QM00486B, Research Article
Yanbin Gong, Kai Chang, Cheng Chen, Mengmeng Han, Xuejun Zhan, Jie Min, Xuechen Jiao, Qianqian Li, Zhen Li
A class of pyrene-fused PDI-NFAs are designed and synthesized for fabricating ternary OSC devices to improve the absorption in the short wavelength region, VOC and thermal stability of the ternary devices.
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12 Nov 05:09

[ASAP] Chemical and Biomolecule Sensing with Organic Field-Effect Transistors

by Hui Li, Wei Shi, Jian Song, Hyun-June Jang, Jennifer Dailey, Junsheng Yu, Howard E. Katz

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Chemical Reviews
DOI: 10.1021/acs.chemrev.8b00016
03 Nov 09:50

Response to Comment on “Charge Carrier Extraction in Organic Solar Cells Governed by Steady‐State Mobilities”

by Vincent M. Le Corre, Azadeh Rahimi Chatri, Nutifafa Y. Doumon, L. Jan Anton Koster
Advanced Energy Materials, Volume 8, Issue 36, December 27, 2018.
03 Nov 09:50

Comment on “Charge Carrier Extraction in Organic Solar Cells Governed by Steady‐State Mobilities”

by Nikolaos Felekidis, Armantas Melianas, Luis E. Aguirre, Martijn Kemerink
Advanced Energy Materials, Volume 8, Issue 36, December 27, 2018.
03 Nov 06:16

[ASAP] Upgrading Cross-Coupling Reactions for Biaryl Syntheses

by Yun-Fei Zhang, Zhang-Jie Shi

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Accounts of Chemical Research
DOI: 10.1021/acs.accounts.8b00408
03 Nov 04:17

[ASAP] The History of Palladium-Catalyzed Cross-Couplings Should Inspire the Future of Catalyst-Transfer Polymerization

by Amanda K. Leone, Emily A. Mueller, Anne J. McNeil

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Journal of the American Chemical Society
DOI: 10.1021/jacs.8b09103
02 Nov 05:51

Why are S–F and S–O non-covalent interactions stabilising?

J. Mater. Chem. C, 2018, 6,12413-12421
DOI: 10.1039/C8TC04252G, Paper
Karl J. Thorley, Iain McCulloch
Dipole alignment of substituents greatly affects the torsional potential between neighbouring rings in conjugated organic materials.
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02 Nov 01:47

[ASAP] Controlled Polymerization of a Cyclopentadithiophene–Phenylene Alternating Copolymer

by Marie-Paule Van Den Eede, Julien De Winter, Pascal Gerbaux, Guy Koeckelberghs

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Macromolecules
DOI: 10.1021/acs.macromol.8b01820
02 Nov 01:41

[ASAP] Thiophene–Vinylene–Thiophene-Based Donor–Acceptor Copolymers with Acetylene-Inserted Branched Alkyl Side Chains To Achieve High Field-Effect Mobilities

by De-Yang Chiou, Yen-Chen Su, Kai-En Hung, Jhih-Yang Hsu, Tze-Gang Hsu, Tung-Yu Wu, Yen-Ju Cheng

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Chemistry of Materials
DOI: 10.1021/acs.chemmater.8b02801
25 Feb 04:20

Carbonyl-Functionalized Cyclazines as Colorants and Air-Stable n-Type Semiconductors

by Artem Skabeev, Ute Zschieschang, Yulian Zagranyarski, Hagen Klauk, Klaus Müllen and Chen Li

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Organic Letters
DOI: 10.1021/acs.orglett.8b00183
21 Feb 09:32

Titanocene-Mediated Dinitrile Coupling: A Divergent Route to Nitrogen-Containing Polycyclic Aromatic Hydrocarbons

by Gavin R. Kiel, Adrian E. Samkian, Amélie Nicolay, Ryan J. Witzke and T. Don Tilley

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Journal of the American Chemical Society
DOI: 10.1021/jacs.7b13823
21 Feb 09:28

A Stable Blue Photosensitizer for Color Palette of Dye-Sensitized Solar Cells Reaching 12.6% Efficiency

by Yameng Ren, Danyang Sun, Yiming Cao, Hoi Nok Tsao, Yi Yuan, Shaik M. Zakeeruddin, Peng Wang and Michael Grätzel

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Journal of the American Chemical Society
DOI: 10.1021/jacs.7b12348
21 Feb 09:12

Fluorescent Cyanine Dye J-Aggregates in the Fluorous Phase

by Wei Cao and Ellen M. Sletten

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Journal of the American Chemical Society
DOI: 10.1021/jacs.7b11925
03 Jan 15:08

A Direct C–H Coupling Method for Preparing π-Conjugated Functional Polymers with High Regioregularity

by Qiang Zhang, Meijia Chang, Yan Lu, Yanna Sun, Chenxi Li, Xinlin Yang, Mingtao Zhang and Yongsheng Chen
KunYang

🍊

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Macromolecules
DOI: 10.1021/acs.macromol.7b02390
26 Dec 13:50

Synthesis and remarkable mechano- and thermo-hypsochromic luminescence of a new type of DPP-based derivative

J. Mater. Chem. C, 2018, 6,1377-1383
DOI: 10.1039/C7TC04698G, Paper
Zhongwei Liu, Kai Zhang, Qikun Sun, Zhenzhen Zhang, Liangliang Tang, Shanfeng Xue, Dongmei Chen, Haichang Zhang, Wenjun Yang
A new DPP dye emits a yellow color in solution but can aggregate into high contrast NIR, red, and yellow solids.
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25 Dec 13:43

Aromaticity switching via azulene transformations in azulene-bridged A,D-dithiahexaphyrin

Chem. Commun., 2017, Accepted Manuscript
DOI: 10.1039/C7CC08754C, Communication
Michal Jacek Bialek, Lechoslaw Latos-Grazynski
The incorporation of an azulene bridge into an aromatic hexaphyrin framework allows to manipulate [small pi]-electron delocalization pathways. The palladium(II) complex undergoes the hydroxyl-triggered azulene contraction or isomerization to an oxynaphthalene...
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25 Dec 13:30

[small pi]-Conjugation expanded isoindigo derivatives and the donor-acceptor conjugated polymers: synthesis and characterization

Chem. Commun., 2017, Accepted Manuscript
DOI: 10.1039/C7CC08603B, Communication
Hao Song, Yunfeng Deng, Yu Jiang, Hongkun Tian, Yanhou Geng
Two [small pi]-conjugation expanded isoindigo derivatives (DIID-PhCO and TIID-PhCO) composed of up to 18 rings and two donor-acceptor conjugated polymers based on DIID-PhCO were synthesized. Both polymers are ambipolar semiconductors with...
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24 Dec 16:04

Relating Structure to Efficiency in Surfactant-Free Polymer/Fullerene Nanoparticle-Based Organic Solar Cells

by Stefan Gärtner, Andrew J. Clulow, Ian A. Howard, Elliot P. Gilbert, Paul L. Burn, Ian R. Gentle and Alexander Colsmann

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ACS Applied Materials & Interfaces
DOI: 10.1021/acsami.7b15601
17 Dec 02:42

Polythiophene: From Fundamental Perspectives to Applications

by Thaneshwor P. Kaloni, Patrick K. Giesbrecht, Georg Schreckenbach and Michael S. Freund

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Chemistry of Materials
DOI: 10.1021/acs.chemmater.7b03035
16 Dec 13:04

Expanded Helicenes: A General Synthetic Strategy and Remarkable Supramolecular and Solid-State Behavior

by Gavin R. Kiel, Sajan C. Patel, Patrick W. Smith, Daniel S. Levine and T. Don Tilley
KunYang

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Journal of the American Chemical Society
DOI: 10.1021/jacs.7b10902
12 Dec 02:03

Incorporation of 2,6-Connected Azulene Units into the Backbone of Conjugated Polymers: Towards High-Performance Organic Optoelectronic Materials

by Xike Gao, Hanshen Xin, Congwu Ge, Xuechen Jiao, Xiaodi Yang, Kira Rundel, Chris McNeill

Abstract

Azulene is a promising candidate for constructing optoelectronic materials. An effective strategy is presented to obtain high-performance conjugated polymers by incorporating 2,6-connected azulene units into the polymeric backbone, and two conjugated copolymers P(TBAzDI-TPD) and P(TBAzDI-TFB) were designed and synthesized based on this strategy. They are the first two examples for 2,6-connected azulene-based conjugated polymers and exhibit unipolar n-type transistor performance with an electron mobility of up to 0.42 cm2 V−1 s−1, which is among the highest values for n-type polymeric semiconductors in bottom-gate top-contact organic field-effect transistors. Preliminary all-polymer solar cell devices with P(TBAzDI-TPD) as the electron acceptor and PTB7-Th as the electron donor display a power conversion efficiency of 1.82 %.

Thumbnail image of graphical abstract

An effective strategy for achieving high-performance polymers in optoelectronic materials by incorporation of 2,6-connected azulene units into the polymeric backbone is presented. Two examples of 2,6-connected azulene-based conjugated polymers were designed and synthesized, with an electron mobility of >0.4 cm2 V−1 s−1 for BGTC OFETs and a power conversion efficiency of >1.8 % for all-polymer solar cells.

11 Dec 01:21

B–N Lewis Pair Functionalization of Anthracene: Structural Dynamics, Optoelectronic Properties, and O2 Sensitization

by Kanglei Liu, Roger A. Lalancette and Frieder Jäkle

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Journal of the American Chemical Society
DOI: 10.1021/jacs.7b11062