Synthesis and Emergent Photophysical Properties of Diketopyrrolopyrrole-Based Supramolecular Self-Assembly

被引:5
作者
Maity, Nilabja [1 ]
Majumder, Kanad [1 ]
Patel, Arun Kumar [2 ]
Swain, Diptikanta [1 ,3 ]
Suryaprakash, Nagarajarao [2 ]
Patil, Satish [1 ]
机构
[1] Indian Inst Sci, Solid State & Struct Chem Unit, Bangalore 560012, India
[2] Indian Inst Sci, NMR Res Ctr, Bangalore 560012, India
[3] Inst Chem Technol, Solid State & Struct Chem Unit, Indian Oil Odisha Campus, Bhubaneswar 751013, India
来源
ACS OMEGA | 2022年 / 7卷 / 27期
基金
英国工程与自然科学研究理事会;
关键词
ORGANIC SEMICONDUCTORS; MOLECULAR RECOGNITION; 2-PHOTON ABSORPTION; COAXIAL NANOTUBES; ENERGY-TRANSPORT; ELECTRON-DONOR; POLYMERS; ORGANIZATION; ACCEPTOR; POLYMERIZATION;
D O I
10.1021/acsomega.2c01091
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Diketopyrrolopyrrole (DPP)-based molecular semiconductors exhibit intriguing optical and charge transport properties. Herein, we rationally design a series of electronically identical but structurally distinct Hamilton receptor (HR)-based supramolecular assembly of DPP. The HR endows supramolecular assemblies via hydrogen bonding with enhanced structural ordering and excitonic couplings. The mechanism of supramolecular self-assembly was probed by diffusion ordered spectroscopy (DOSY) nuclear magnetic resonance (NMR) and solid-state IR spectroscopy studies. We investigated the morphology of self-assembly, photophysical and electrochemical properties and compared them with the identical DPP molecular structures without HRs. The microstructure of self-assembly was probed with atomic force microscopy in thin films. Subsequently, the influence of solid-state packing was studied by single-crystal X-ray diffraction. The single-crystal structure of HR-TDPP-C-20 reveals slipped stack arrangements between the two neighboring chromophores with pi-pi stacking distance and slip angle of 3.55 angstrom and 35.4 degrees, respectively. Notably, the slight torsional angle of 1 degrees between thiophene and lactam rings and small pi-pi stacking distance suggest a significant intermolecular coupling between thiophene (D) and lactam (A) rings. This intramolecular coupling between two pi-pi chromophore stacks manifests in their optical properties. In this manuscript, we report rational design and synthesis of supramolecular self-assembly of DPP with a collection of compelling structural and optical properties.
引用
收藏
页码:23179 / 23188
页数:10
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