Facile Azabenz‐Annulations through UV‐induced Photocyclization: A promising method for Perylenediimide‐Based Organic Semiconductors

Towards a Tangible Philosophy through Design

Conference Proceedings of the Academy for Design Innovation Management ◽

10.33114/adim.2019.02.195 ◽

2019 ◽

Vol 2 (1) ◽

Author(s):

Jelle VAN DIJK ◽

Jonne VAN BELLE ◽

Wouter EGGINK

Keyword(s):

Digital Age ◽

Promising Method ◽

Design Approach ◽

The World ◽

First Results

The combined philosophy and design approach called Philosophy-through-Design (PtD) is proposed using an exemplary project about being-in-the-world in the digital age. PtD is a practical way to do philosophy through designing interventions, and involves various people in the exploration of philosophical concepts. It stems from the overlapping questions found in philosophy and design regarding human-technology interaction. By intertwining both, they benefit from describing, understanding and proposing human-technology interactions to unfold new questions and perspectives. In the exemplary project, being-in-the-world refers to a way of being that is embodied, active, open-ended and situational, based on the phenomenological and embodied theories of Tim Ingold. This concept questions what it means to be human in the digital age and how our lives with technology are built. The first results show the process of weaving together observation, creation and reflection, which presents Philosophy-through-Design as a promising method for designers to practice a tangible philosophy.

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Energetic Control of Redox-Active Polymers Towards Safe Organic Bioelectronic Materials

10.26434/chemrxiv.11366186.v1 ◽

2019 ◽

Author(s):

Alexander Giovannitti ◽

Reem B. Rashid ◽

Quentin Thiburce ◽

Bryan D. Paulsen ◽

Camila Cendra ◽

...

Keyword(s):

Molecular Oxygen ◽

Organic Semiconductors ◽

Side Reaction ◽

Semiconducting Polymers ◽

Side Reactions ◽

Redox Active ◽

Donor Acceptor ◽

Electrochemical Devices ◽

Biological Environment ◽

Device Operation

Avoiding faradaic side reactions during the operation of electrochemical devices is important to enhance the device stability, to achieve low power consumption, and to prevent the formation of reactive side‑products. This is particularly important for bioelectronic devices which are designed to operate in biological systems. While redox‑active materials based on conducting and semiconducting polymers represent an exciting class of materials for bioelectronic devices, they are susceptible to electrochemical side‑reactions with molecular oxygen during device operation. We show that this electrochemical side reaction yields hydrogen peroxide (H2O2), a reactive side‑product, which may be harmful to the local biological environment and may also accelerate device degradation. We report a design strategy for the development of redox-active organic semiconductors based on donor-acceptor copolymers that prevent the formation of H2O2 during device operation. This study elucidates the previously overlooked side-reactions between redox-active conjugated polymers and molecular oxygen in electrochemical devices for bioelectronics, which is critical for the operation of electrolyte‑gated devices in application-relevant environments.

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Quantitative Image Analysis of Fractal-like Thin Films of Organic Semiconductors

10.26434/chemrxiv.6223610.v1 ◽

2018 ◽

Author(s):

Weikun Zhu ◽

Erfan Mohammadi ◽

Ying Diao

Keyword(s):

Thin Film ◽

Thin Films ◽

Image Analysis ◽

Fractal Dimension ◽

Organic Semiconductors ◽

Film Growth ◽

Electronic Device ◽

Significant Control ◽

Semiconductor Thin Films ◽

Two Parameters

Morphology modulation offers significant control over organic electronic device performance. However, morphology quantification has been rarely carried out via image analysis. In this work, we designed a MATLAB program to evaluate two key parameters describing morphology of small molecule semiconductor thin films: fractal dimension and film coverage. We then employ this program in a case study of meniscus-guided coating of 2,7-dioctyl[1]benzothieno[3,2-b][1]benzothiophene (C8-BTBT) under various conditions to analyze a diverse and complex morphology set. The evolution of morphology in terms of fractal dimension and film coverage was studied as a function of coating speed. We discovered that combined fractal dimension and film coverage can quantitatively capture the key characteristics of C8-BTBT thin film morphology; change of these two parameters further inform morphology transition. Furthermore, fractal dimension could potentially shed light on thin film growth mechanisms.

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Design and Synthesis of Two-Dimensional Covalent Organic Frameworks with Four-Arm Cores: Prediction of Remarkable Ambipolar Charge-Transport Properties

10.26434/chemrxiv.7766786.v2 ◽

2019 ◽

Author(s):

Simil Thomas ◽

Hong Li ◽

Raghunath R. Dasari ◽

Austin Evans ◽

William Dichtel ◽

...

Keyword(s):

Charge Transport ◽

Organic Semiconductors ◽

Density Functional ◽

Polymer Networks ◽

Two Dimensional ◽

Covalent Organic Frameworks ◽

X Ray Diffraction ◽

Zinc Porphyrin ◽

Design And Synthesis ◽

Predicted Values

We have considered three two-dimensional (2D) π-conjugated polymer networks (i.e., covalent organic frameworks, COFs) materials based on pyrene, porphyrin, and zinc-porphyrin cores connected via diacetylenic linkers. Their electronic structures, investigated at the density functional theory global-hybrid level, are indicative of valence and conduction bands that have large widths, ranging between 1 and 2 eV. Using a molecular approach to derive the electronic couplings between adjacent core units and the electron-vibration couplings, the three π-conjugated 2D COFs are predicted to have ambipolar charge-transport characteristics with electron and hole mobilities in the range of 65-95 cm2V-1s-1. Such predicted values rank these 2D COFs among the highest-mobility organic semiconductors. In addition, we have synthesized the zinc-porphyrin based 2D COF and carried out structural characterization via powder X-ray diffraction and surface area analysis, which demonstrates the feasability of these electroactive networks.

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