pH-Directed Aggregation to Control Photoconductivity in Self-Assembled Perylene Bisimides

被引：55

作者：

Draper, Emily R. ^{[1
,2
]}

Greeves, Benjamin J. ^{[2
]}

Barrow, Michael ^{[2
]}

Schweins, Ralf ^{[3
]}

Zwijnenburg, Martijn A. ^{[4
]}

Adams, Dave J. ^{[1
,2
]}

机构：

[1] Univ Glasgow, Sch Chem, WESTChem, Glasgow G12 8QQ, Lanark, Scotland

[2] Univ Liverpool, Dept Chem, Crown St, Liverpool L69 7ZD, Merseyside, England

[3] Large Scale Struct Grp, Inst Laue Langevin, 71 Ave Martyrs,CS 20156, F-38042 Grenoble 9, France

[4] UCL, Dept Chem, 20 Gordon St, London WC1H 0AJ, England

来源：

CHEM | 2017年 / 2卷 / 05期

基金：

英国工程与自然科学研究理事会; 美国国家科学基金会;

关键词：

ELECTRONIC-STRUCTURE; LIQUID-CRYSTALLINE; MOLECULAR-STRUCTURE; AQUEOUS-MEDIA; DIIMIDES; DERIVATIVES; WATER; DYES; TRANSFORMATION; GENERATION;

D O I：

10.1016/j.chempr.2017.03.022

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Perylene bisimides (PBIs) are one example of useful p-conjugated molecules that can be used in optoelectronic devices as n-type materials with strong visible light absorption. PBIs can self-assemble into a range of structures, but it is rare to be able to control the packing such that the same PBI can form either H-type or J-type aggregates. This is important because the conductivity pathways and optoelectronic properties are directly affected by this packing. Here, we show that we can control the packing of a single PBI functionalized with an amino acid by a subtle change in pH. Under one set of conditions, H-type aggregates form a gel when the pH is decreased. At a slightly different set of starting conditions, J-type aggregates are formed, but they cannot form a gel when the pH is lowered. We show that films formed from the self-assembled structures have very different photoconductive properties.

引用

页码：716 / 731

页数：16

共 61 条

[11] Aligning self-assembled gelators by drying under shear [J].

Draper, Emily R. ;

Mykhaylyk, Oleksandr O. ;

Adams, Dave J. .

CHEMICAL COMMUNICATIONS, 2016, 52 (42) :6934-6937

[12] Air-stable photoconductive films formed from perylene bisimide gelators [J].

Draper, Emily R. ;

Walsh, James J. ;

McDonald, Tom O. ;

Zwijnenburg, Martijn A. ;

Cameron, Petra J. ;

Cowan, Alexander J. ;

Adams, Dave J. .

JOURNAL OF MATERIALS CHEMISTRY C, 2014, 2 (28) :5570-5575

[13] Assembly Modulation of PDI Derivative as a Supramolecular Fluorescence Switching Probe for Detection of Cationic Surfactant and Metal Ions in Aqueous Media [J].

Dwivedi, Atul K. ;

Pandeeswar, M. ;

Govindaraju, T. .

ACS APPLIED MATERIALS & INTERFACES, 2014, 6 (23) :21369-21379

[14]

Frisch M. J., 2016, Gaussian 16 Rev. B.01

[15] Turbomole [J].

Furche, Filipp ;

Ahlrichs, Reinhart ;

Haettig, Christof ;

Klopper, Wim ;

Sierka, Marek ;

Weigend, Florian .

WILEY INTERDISCIPLINARY REVIEWS-COMPUTATIONAL MOLECULAR SCIENCE, 2014, 4 (02) :91-100

[16] Control of H- and J-Type π Stacking by Peripheral Alkyl Chains and Self-Sorting Phenomena in Perylene Bisimide Homo- and Heteroaggregates [J].

Ghosh, Suhrit ;

Li, Xue-Qing ;

Stepanenko, Vladimir ;

Wuerthner, Frank .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (36) :11343-11357

[17] Molecular Assemblies of Perylene Bisimide Dyes in Water [J].

Goerl, Daniel ;

Zhang, Xin ;

Wuerthner, Frank .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (26) :6328-6348

[18] Reversible Switching between Molecular and Charge Transfer Phases in a Liquid Crystalline Organic Semiconductor [J].

Gregg, Brian A. ;

Kose, Muhammet Erkan .

CHEMISTRY OF MATERIALS, 2008, 20 (16) :5235-5239

[19] Consistent structures and interactions by density functional theory with small atomic orbital basis sets [J].

Grimme, Stefan ;

Brandenburg, Jan Gerit ;

Bannwarth, Christoph ;

Hansen, Andreas .

JOURNAL OF CHEMICAL PHYSICS, 2015, 143 (05)

[20] Interference between Coulombic and CT-mediated couplings in molecular aggregates: H- to J-aggregate transformation in perylene-based π-stacks [J].

Hestand, Nicholas J. ;

Spano, Frank C. .

JOURNAL OF CHEMICAL PHYSICS, 2015, 143 (24)

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