Accelerated Discovery of High-Refractive-Index Polyimides via First-Principles Molecular Modeling, Virtual High-Throughput Screening, and Data Mining

We present a high-throughput computational study to identify novel polyimides (PIs) with exceptional refractive index (RI) values for use as optic or optoelectronic materials. Our study utilizes an RI prediction protocol based on a combination of first-principles and data modeling developed in previous work, which we employ on a large-scale PI candidate library generated with the ChemLG code. We deploy the virtual screening software ChemHTPS to automate the assessment of this extensive pool of PI structures in order to determine the performance potential of each candidate. This rapid and efficient approach yields a number of highly promising lead compounds. Using the data mining and machine learning program package ChemML, we analyze the top candidates with respect to prevalent structural features and feature combinations that distinguish them from less promising ones. In particular, we explore the utility of various strategies that introduce highly polarizable moieties into the PI backbone to increase it...

[1]  Francois Kajzar,et al.  Optical control of an integrated interferometer using a photochromic polymer , 2001 .

[2]  W. Goddard,et al.  UFF, a full periodic table force field for molecular mechanics and molecular dynamics simulations , 1992 .

[3]  Alán Aspuru-Guzik,et al.  Accelerated computational discovery of high-performance materials for organic photovoltaics by means of cheminformatics , 2011 .

[4]  Martha I. Sanchez,et al.  Nanoporous Polyimides Derived from Highly Fluorinated Polyimide/Poly(propylene Oxide) Copolymers , 2001 .

[5]  A. Askadskii,et al.  The Packing of polymer molecules , 1970 .

[6]  Nancy Wilkins-Diehr,et al.  NSF’s Inaugural Software Institutes: The Science Gateways Community Institute and the Molecular Sciences Software Institute , 2018, Computing in Science & Engineering.

[7]  Jian Pei,et al.  Roles of Flexible Chains in Organic Semiconducting Materials , 2014 .

[8]  Alán Aspuru-Guzik,et al.  Theoretical Characterization of the Air-Stable, High-Mobility Dinaphtho[2,3-b:2′3′-f]thieno[3,2-b]-thiophene Organic Semiconductor , 2010, The Journal of Physical Chemistry C.

[9]  Chao‐Ching Chang,et al.  Synthesis and Optical Properties of Soluble Polyimide/Titania Hybrid Thin Films , 2006 .

[10]  Alán Aspuru-Guzik,et al.  The Harvard Clean Energy Project: Large-Scale Computational Screening and Design of Organic Photovoltaics on the World Community Grid , 2011 .

[11]  Mojtaba Haghighatlari,et al.  Advances of machine learning in molecular modeling and simulation , 2019, Current Opinion in Chemical Engineering.

[12]  Chia-Liang Tsai,et al.  Highly transparent polyimide hybrids for optoelectronic applications , 2016 .

[13]  Mohammad Atif Faiz Afzal,et al.  Building and deploying a cyberinfrastructure for the data-driven design of chemical systems and the exploration of chemical space , 2018 .

[14]  S. Grimme,et al.  A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu. , 2010, The Journal of chemical physics.

[15]  F. Krebs,et al.  Organic photovoltaics , 2013, Nanotechnology.

[16]  Cecilia Clementi,et al.  Perspective: Computational chemistry software and its advancement as illustrated through three grand challenge cases for molecular science. , 2018, The Journal of chemical physics.

[17]  Mohini Sain,et al.  Development of transparent bacterial cellulose nanocomposite film as substrate for flexible organic light emitting diode (OLED) display , 2012 .

[18]  Shinji Ando,et al.  Synthesis, characterization, and optical properties of metal-containing fluorinated polyimide films , 1998 .

[19]  Frank Neese,et al.  The ORCA program system , 2012 .

[20]  Hyunsu Cho,et al.  A Facile Route to Efficient, Low‐Cost Flexible Organic Light‐Emitting Diodes: Utilizing the High Refractive Index and Built‐In Scattering Properties of Industrial‐Grade PEN Substrates , 2015, Advanced materials.

[21]  Alán Aspuru-Guzik,et al.  What Is High-Throughput Virtual Screening? A Perspective from Organic Materials Discovery , 2015 .

[22]  G. Odian,et al.  Principles of polymerization , 1981 .

[23]  Chris Morley,et al.  Open Babel: An open chemical toolbox , 2011, J. Cheminformatics.

[24]  Gabi Gruetzner,et al.  New inks for the direct drop-on-demand fabrication of polymer lenses , 2011 .

[25]  Jingang Liu,et al.  High refractive index polymers: fundamental research and practical applications , 2009 .

[26]  Sridhar Krishnaswamy,et al.  Direct Laser Writing Polymer Micro-Resonators for Refractive Index Sensors , 2016, IEEE Photonics Technology Letters.

[27]  Chong Cheng,et al.  Combining first-principles and data modeling for the accurate prediction of the refractive index of organic polymers. , 2018, The Journal of chemical physics.

[28]  Junji Nishii,et al.  Microlens arrays of high-refractive-index glass fabricated by femtosecond laser lithography , 2009 .

[29]  Maria Bruma,et al.  Influence of Chemical Structure on the Refractive Index of Imide‐Type Polymers , 2013 .

[30]  Chang-Ki Moon,et al.  Highly Enhanced Light Extraction from Surface Plasmonic Loss Minimized Organic Light‐Emitting Diodes , 2013, Advanced materials.

[31]  M. Afzal.  From Virtual High-Throughput Screening and Machine Learning to the Discovery and Rational Design of Polymers for Optical Applications , 2018 .

[32]  Osamu Moriya,et al.  Novel materials for large change in refractive index : Synthesis and photochemical reaction of the ladderlike poly(silsesquioxane) containing norbornadiene, azobenzene, and anthracene groups in the side chains , 2006 .

[33]  Y. Kokubun,et al.  Athermal waveguides for temperature-independent lightwave devices , 1993, IEEE Photonics Technology Letters.

[34]  Tomoya Higashihara,et al.  Recent Progress in High Refractive Index Polymers , 2015 .

[35]  Shinji Ando,et al.  Synthesis and properties of highly refractive polyimides derived from fluorene‐bridged sulfur‐containing dianhydrides and diamines , 2008 .

[36]  Nicola Cioffi,et al.  Carbon based materials for electronic bio-sensing , 2011 .

[37]  Shinji Ando,et al.  Synthesis of High Refractive Index Polyimides Derived from 1,6-Bis(p-aminophenylsulfanyl)-3,4,8,9-tetrahydro-2,5,7,10-tetrathiaanthracene and Aromatic Dianhydrides , 2008 .

[38]  Dominique Verreault,et al.  Synthesis and characterization of novel, soluble sulfur-containing copolyimides with high refractive indices , 2011 .

[39]  Shinji Ando,et al.  Optically Transparent Sulfur-Containing Polyimide−TiO2 Nanocomposite Films with High Refractive Index and Negative Pattern Formation from Poly(amic acid)−TiO2 Nanocomposite Film , 2009 .

[40]  Richard F. Haglund,et al.  Anti-reflective polymer-nanocomposite coatings fabricated by RIR-MAPLE , 2013, Photonics West - Lasers and Applications in Science and Engineering.

[41]  Luping Yu,et al.  Novel aromatic polyimides for nonlinear optics , 1995 .

[42]  Shinji Ando,et al.  Synthesis and Characterization of Highly Refractive Polyimides Derived from Thiophene-Containing Aromatic Diamines and Aromatic Dianhydrides , 2010 .

[43]  F. Weigend,et al.  Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy. , 2005, Physical chemistry chemical physics : PCCP.

[44]  Bon-Cheol Ku,et al.  Synthesis and characterization of high refractive index polyimides derived from 2,5‐Bis(4‐Aminophenylenesulfanyl)‐3,4‐Ethylenedithiothiophene and aromatic dianhydrides , 2015 .

[45]  J. Hachmann,et al.  Benchmarking DFT approaches for the calculation of polarizability inputs for refractive index predictions in organic polymers. , 2019, Physical chemistry chemical physics : PCCP.

[46]  Chang-Sik Ha,et al.  Synthesis, characterization, and properties of fully aliphatic polyimides and their derivatives for microelectronics and optoelectronics applications , 2007 .

[47]  Alán Aspuru-Guzik,et al.  Lead candidates for high-performance organic photovoltaics from high-throughput quantum chemistry – the Harvard Clean Energy Project , 2014 .

[48]  V. Barone,et al.  Toward reliable density functional methods without adjustable parameters: The PBE0 model , 1999 .

[49]  Alán Aspuru-Guzik,et al.  From computational discovery to experimental characterization of a high hole mobility organic crystal , 2011, Nature communications.

[50]  J. Kobayashi,et al.  Fluorinated polyimide waveguides with low polarization-dependent loss and their applications to thermooptic switches , 1998 .

[51]  Stefanie A. Sydlik,et al.  Triptycene Polyimides: Soluble Polymers with High Thermal Stability and Low Refractive Indices , 2011 .

[52]  Alán Aspuru-Guzik,et al.  The Harvard organic photovoltaic dataset , 2016, Scientific Data.

[53]  Valery P. Privalko,et al.  Molecular packing density in the crystalline state of semi‐rigid chain polymers. I: Polyimides , 1997 .

[54]  Shinji Ando,et al.  Synthesis and Characterization of High Refractive Index Polyimides Derived from 4,4′-( p -Phenylenedisulfanyl)dianiline and Various Aromatic Tetracarboxylic Dianhydrides , 2007 .

[55]  Shahram Mehdipour-Ataei,et al.  Synthesis, characterization, and thermal properties of novel arylene sulfone ether polyimides and polyamides , 2000 .