skip to main content
DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

This content will become publicly available on June 6, 2020

Title: Directed polymorphism and mechanofluorochromism of conjugated materials through weak non-covalent control

Abstract

Understanding and manipulating crystal polymorphism can provide novel strategies for materials discovery in organic optoelectronics.

Authors:
ORCiD logo [1];  [1];  [2];  [1]; ORCiD logo [2]; ORCiD logo [1]
  1. Department of Chemistry, Tufts University, Medford, USA
  2. Department of Chemical & Biomolecular Engineering, University of Connecticut, Storrs, USA
Publication Date:
Sponsoring Org.:
USDOE Office of Science (SC), Biological and Environmental Research (BER) (SC-23); USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1527209
Grant/Contract Number:  
SC0012704; KP1605010; SC0016423
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
Journal of Materials Chemistry C
Additional Journal Information:
Journal Name: Journal of Materials Chemistry C Journal Volume: 7 Journal Issue: 27; Journal ID: ISSN 2050-7526
Publisher:
Royal Society of Chemistry (RSC)
Country of Publication:
United Kingdom
Language:
English

Citation Formats

Sharber, Seth A., Mann, Arielle, Shih, Kuo-Chih, Mullin, William J., Nieh, Mu-Ping, and Thomas, Samuel W. Directed polymorphism and mechanofluorochromism of conjugated materials through weak non-covalent control. United Kingdom: N. p., 2019. Web. doi:10.1039/C9TC01301F.
Sharber, Seth A., Mann, Arielle, Shih, Kuo-Chih, Mullin, William J., Nieh, Mu-Ping, & Thomas, Samuel W. Directed polymorphism and mechanofluorochromism of conjugated materials through weak non-covalent control. United Kingdom. doi:10.1039/C9TC01301F.
Sharber, Seth A., Mann, Arielle, Shih, Kuo-Chih, Mullin, William J., Nieh, Mu-Ping, and Thomas, Samuel W. Thu . "Directed polymorphism and mechanofluorochromism of conjugated materials through weak non-covalent control". United Kingdom. doi:10.1039/C9TC01301F.
@article{osti_1527209,
title = {Directed polymorphism and mechanofluorochromism of conjugated materials through weak non-covalent control},
author = {Sharber, Seth A. and Mann, Arielle and Shih, Kuo-Chih and Mullin, William J. and Nieh, Mu-Ping and Thomas, Samuel W.},
abstractNote = {Understanding and manipulating crystal polymorphism can provide novel strategies for materials discovery in organic optoelectronics.},
doi = {10.1039/C9TC01301F},
journal = {Journal of Materials Chemistry C},
number = 27,
volume = 7,
place = {United Kingdom},
year = {2019},
month = {7}
}

Journal Article:
Free Publicly Available Full Text
This content will become publicly available on June 6, 2020
Publisher's Version of Record

Save / Share:

Works referenced in this record:

High contrast stimuli-responsive luminescence switching of pyrene-1-carboxylic esters triggered by a crystal-to-crystal transition
journal, January 2017

  • Kong, Qunshou; Zhuang, Weihua; Li, Gaocan
  • New Journal of Chemistry, Vol. 41, Issue 22
  • DOI: 10.1039/C7NJ03014B

Alkyl length effects on solid-state fluorescence and mechanochromic behavior of small organic luminophores
journal, January 2016

  • Xue, Shanfeng; Qiu, Xu; Sun, Qikun
  • Journal of Materials Chemistry C, Vol. 4, Issue 8
  • DOI: 10.1039/C5TC04358A

A survey of Hammett substituent constants and resonance and field parameters
journal, March 1991

  • Hansch, Corwin.; Leo, A.; Taft, R. W.
  • Chemical Reviews, Vol. 91, Issue 2
  • DOI: 10.1021/cr00002a004

Reversible mechanofluorochromism of aniline-terminated phenylene ethynylenes
journal, January 2018

  • Sharber, Seth A.; Shih, Kuo-Chih; Mann, Arielle
  • Chemical Science, Vol. 9, Issue 24
  • DOI: 10.1039/C8SC00980E

Effective structural modification of traditional fluorophores to obtain organic mechanofluorochromic molecules
journal, January 2018

  • Huang, Xiaobo; Qian, Lebin; Zhou, Yibin
  • Journal of Materials Chemistry C, Vol. 6, Issue 19
  • DOI: 10.1039/C8TC00043C

Substituent Effects That Control Conjugated Oligomer Conformation through Non-covalent Interactions
journal, March 2017

  • Sharber, Seth A.; Baral, Rom Nath; Frausto, Fanny
  • Journal of the American Chemical Society, Vol. 139, Issue 14
  • DOI: 10.1021/jacs.7b00878

Polymorphism-Dependent and Switchable Emission of Butterfly-Like Bis(diarylmethylene)dihydroanthracenes
journal, September 2015


Reversible piezochromic luminescence of 9,10-bis[(N-alkylcarbazol-3-yl)vinyl]anthracenes and the dependence on N-alkyl chain length
journal, January 2013

  • Wang, Yalong; Liu, Wei; Bu, Lingyu
  • J. Mater. Chem. C, Vol. 1, Issue 4
  • DOI: 10.1039/C2TC00470D

Mechano-Responsive Luminescence via Crystal-to-Crystal Phase Transitions between Chiral and Non-Chiral Space Groups
journal, May 2017

  • Jin, Mingoo; Seki, Tomohiro; Ito, Hajime
  • Journal of the American Chemical Society, Vol. 139, Issue 22
  • DOI: 10.1021/jacs.7b04073

Mechanoresponsive Luminescent Molecular Assemblies: An Emerging Class of Materials
journal, October 2015

  • Sagara, Yoshimitsu; Yamane, Shogo; Mitani, Masato
  • Advanced Materials, Vol. 28, Issue 6
  • DOI: 10.1002/adma.201502589

Predicting polymorphism in molecular crystals using orientational entropy
journal, September 2018

  • Piaggi, Pablo M.; Parrinello, Michele
  • Proceedings of the National Academy of Sciences, Vol. 115, Issue 41
  • DOI: 10.1073/pnas.1811056115

Building upon Supramolecular Synthons: Some Aspects of Crystal Engineering
journal, May 2015


Three polymorphs of one luminogen: how the molecular packing affects the RTP and AIE properties?
journal, January 2017

  • Yang, Jie; Ren, Zichun; Chen, Bin
  • Journal of Materials Chemistry C, Vol. 5, Issue 36
  • DOI: 10.1039/C7TC03656F

Modulating Mechanochromic Luminescence Quenching of Alkylated Iodo Difluoroboron Dibenzoylmethane Materials
journal, June 2016

  • Morris, William A.; Sabat, Michal; Butler, Tristan
  • The Journal of Physical Chemistry C, Vol. 120, Issue 26
  • DOI: 10.1021/acs.jpcc.6b03239

Conformational Control of Oligo( p -phenyleneethynylene)s with Intrinsic Substituent Electronic Effects: Origin of the Twist in Pentiptycene-Containing Systems
journal, September 2014

  • Lin, Che-Jen; Kundu, Sandip Kumar; Lin, Cheng-Kai
  • Chemistry - A European Journal, Vol. 20, Issue 45
  • DOI: 10.1002/chem.201403795

Structure–mechanical property correlations in mechanochromic luminescent crystals of boron difluoride dibenzoylmethane derivatives
journal, September 2015


Halogen bonding in polymer science: from crystal engineering to functional supramolecular polymers and materials
journal, January 2015

  • Berger, Gilles; Soubhye, Jalal; Meyer, Franck
  • Polymer Chemistry, Vol. 6, Issue 19
  • DOI: 10.1039/C5PY00354G

Molecular Engineering of Mechanochromic Materials by Programmed C–H Arylation: Making a Counterpoint in the Chromism Trend
journal, September 2016

  • Wu, Jie; Cheng, Yangyang; Lan, Jingbo
  • Journal of the American Chemical Society, Vol. 138, Issue 39
  • DOI: 10.1021/jacs.6b03890

Polymorphism-dependent aggregation induced emission of a push–pull dye and its multi-stimuli responsive behavior
journal, January 2016

  • Botta, Chiara; Benedini, Sara; Carlucci, Lucia
  • Journal of Materials Chemistry C, Vol. 4, Issue 14
  • DOI: 10.1039/C5TC03352G

Tricolor Luminescence Switching by Thermal and Mechanical Stimuli in the Crystal Polymorphs of Pyridyl-substituted Fluorene
journal, December 2018

  • Guan, Jianping; Xu, Fan; Tian, Chang
  • Chemistry - An Asian Journal, Vol. 14, Issue 1
  • DOI: 10.1002/asia.201801476

Presence of Short Intermolecular Contacts Screens for Kinetic Stability in Packing Polymorphs
journal, May 2018

  • Purdum, Geoffrey E.; Telesz, Nicholas G.; Jarolimek, Karol
  • Journal of the American Chemical Society, Vol. 140, Issue 24
  • DOI: 10.1021/jacs.8b01421

Alkyl chain length effects on solid-state difluoroboron β-diketonate mechanochromic luminescence
journal, January 2011

  • Nguyen, Nguyen D.; Zhang, Guoqing; Lu, Jiwei
  • Journal of Materials Chemistry, Vol. 21, Issue 23
  • DOI: 10.1039/c1jm00067e

Controlling solid-state optical properties of stimuli responsive dimethylamino-substituted dibenzoylmethane materials
journal, January 2017

  • Butler, Tristan; Wang, Fang; Sabat, Michal
  • Materials Chemistry Frontiers, Vol. 1, Issue 9
  • DOI: 10.1039/C7QM00157F

Crystal Engineering: A Holistic View
journal, November 2007

  • Desiraju, Gautam R.
  • Angewandte Chemie International Edition, Vol. 46, Issue 44
  • DOI: 10.1002/anie.200700534

Non-covalent routes to tune the optical properties of molecular materials
journal, January 2014

  • Varughese, Sunil
  • Journal of Materials Chemistry C, Vol. 2, Issue 18
  • DOI: 10.1039/c3tc32414a

Symmetry Influence on the Rotation of Molecules in Crystals
journal, August 2017

  • Islamov, Daut R.; Shtyrlin, Valery G.; Serov, Nikita Yu.
  • Crystal Growth & Design, Vol. 17, Issue 9
  • DOI: 10.1021/acs.cgd.7b00588

Polymorphism in Molecular Solids: An Extraordinary System of Red, Orange, and Yellow Crystals
journal, September 2010


Reversible luminescence color switching in the crystal polymorphs of 2,7-bis(2′-methyl-[1,1′-biphenyl]-4-yl)-fluorenone by thermal and mechanical stimuli
journal, January 2016

  • Du, Xianchao; Xu, Fan; Yuan, Mao-Sen
  • Journal of Materials Chemistry C, Vol. 4, Issue 37
  • DOI: 10.1039/C6TC02804G

Crystal Engineering: From Molecule to Crystal
journal, June 2013

  • Desiraju, Gautam R.
  • Journal of the American Chemical Society, Vol. 135, Issue 27
  • DOI: 10.1021/ja403264c

Aggregation-Induced Emission: Together We Shine, United We Soar!
journal, October 2015


Utilization of the Perfluoroarene-Arene Interaction for Stabilization of Liquid Crystal Phases
journal, September 2012


Mechanochromic and thermochromic fluorescent properties of cyanostilbene derivatives
journal, September 2013


Organic Polymorphs: One-Compound-Based Crystals with Molecular-Conformation- and Packing-Dependent Luminescent Properties
journal, July 2014


Polymorphism-dependent and piezochromic luminescence based on molecular packing of a conjugated molecule
journal, January 2014


Polymorphism and mechanochromism of N-alkylated 1,4-dihydropyridine derivatives containing different electron-withdrawing end groups
journal, January 2017

  • Lei, Yunxiang; Zhou, Yibin; Qian, Lebin
  • Journal of Materials Chemistry C, Vol. 5, Issue 21
  • DOI: 10.1039/C7TC00362E

Twisting and piezochromism of phenylene-ethynylenes with aromatic interactions between side chains and main chains
journal, January 2014

  • Pawle, R. H.; Haas, T. E.; Müller, P.
  • Chem. Sci., Vol. 5, Issue 11
  • DOI: 10.1039/C4SC01466A

Molecular-Level Understanding of Structural Changes of Organic Crystals Induced by Macroscopic Mechanical Stimulation
journal, January 2016


Significant effect of alkyl chain length on fluorescent thermochromism of 9,10-bis(p-alkoxystyryl)anthracenes
journal, January 2015

  • Xiong, Yao; Ma, Yawen; Yan, Xilong
  • RSC Advances, Vol. 5, Issue 66
  • DOI: 10.1039/C5RA08809G

Visualization of Single-Crystal-to-Single-Crystal Phase Transition of Luminescent Molecular Polymorphs
journal, June 2018


Multifunctional organic fluorescent materials derived from 9,10-distyrylanthracene with alkoxyl endgroups of various lengths
journal, January 2012

  • Zhang, Xiqi; Chi, Zhenguo; Xu, Bingjia
  • Chemical Communications, Vol. 48, Issue 88
  • DOI: 10.1039/c2cc36263e

On the validity of Wallach's rule: on the density and stability of racemic crystals compared with their chiral counterparts
journal, December 1991

  • Brock, Carolyn Pratt; Schweizer, W. Bernd; Dunitz, Jack D.
  • Journal of the American Chemical Society, Vol. 113, Issue 26
  • DOI: 10.1021/ja00026a015

Tunable and Switchable Solid State Fluorescence: Alkyl Chain Length-Dependent Molecular Conformation and Self-Reversible Thermochromism
journal, September 2017

  • Hariharan, Palamarneri Sivaraman; Gayathri, Parthasarathy; Moon, Dohyun
  • ChemistrySelect, Vol. 2, Issue 26
  • DOI: 10.1002/slct.201701550

Phase transitions in molecular crystals from a chemical viewpoint
journal, January 1991


Noncovalent Intermolecular Interactions in Organic Electronic Materials: Implications for the Molecular Packing vs Electronic Properties of Acenes
journal, November 2015


Small Changes With Big Consequences: Swapping Two Atoms In Side Chains Changes Phenylene‐Ethynylene Packing And Fluorescence
journal, July 2018

  • Sharber, Seth A.; Thomas, Samuel W.
  • Chemistry – A European Journal, Vol. 24, Issue 64
  • DOI: 10.1002/chem.201804648

Structural landscape of benzoic acid: using experimental crystal structures of fluorobenzoic acids as a probe
journal, January 2012

  • Dubey, Ritesh; Pavan, Mysore S.; Desiraju, Gautam R.
  • Chemical Communications, Vol. 48, Issue 72
  • DOI: 10.1039/c2cc33811d

Functional materials discovery using energy–structure–function maps
journal, March 2017

  • Pulido, Angeles; Chen, Linjiang; Kaczorowski, Tomasz
  • Nature, Vol. 543, Issue 7647
  • DOI: 10.1038/nature21419

Design strategies for organic semiconductors beyond the molecular formula
journal, August 2012

  • Henson, Zachary B.; Müllen, Klaus; Bazan, Guillermo C.
  • Nature Chemistry, Vol. 4, Issue 9
  • DOI: 10.1038/nchem.1422

Polymorphism and Reversible Mechanochromic Luminescence for Solid-State Difluoroboron Avobenzone
journal, February 2010

  • Zhang, Guoqing; Lu, Jiwei; Sabat, Michal
  • Journal of the American Chemical Society, Vol. 132, Issue 7
  • DOI: 10.1021/ja9097719

Material Design for Piezochromic Luminescence:  Hydrogen-Bond-Directed Assemblies of a Pyrene Derivative
journal, February 2007

  • Sagara, Yoshimitsu; Mutai, Toshiki; Yoshikawa, Isao
  • Journal of the American Chemical Society, Vol. 129, Issue 6
  • DOI: 10.1021/ja0677362

UV-induced fluorescence recovery and solubility modulation of photocaged conjugated oligomers
journal, January 2011

  • Pawle, Robert H.; Eastman, Victoria; Thomas, Samuel W.
  • Journal of Materials Chemistry, Vol. 21, Issue 36
  • DOI: 10.1039/c1jm12542g

Side-Chain Liquid Crystalline Polyacetylenes with Increasing Length of Alkyl Tails: From Highly Ordered Smectic to Smectic C Phase
journal, January 2013

  • Yu, Zhen-Qiang; Lam, Jacky W. Y.; Zhu, Cai-Zhen
  • Macromolecules, Vol. 46, Issue 3
  • DOI: 10.1021/ma302540k

Drastic Modulation of Stimuli-Responsive Fluorescence by a Subtle Structural Change of Organic Fluorophore and Polymorphism Controlled Mechanofluorochromism
journal, May 2018

  • Hariharan, Palamarneri Sivaraman; Parthasarathy, Gayathri; Kundu, Anu
  • Crystal Growth & Design, Vol. 18, Issue 7
  • DOI: 10.1021/acs.cgd.8b00310

Synthesis, aggregation-enhanced emission, polymorphism and piezochromism of TPE-cored foldamers with through-space conjugation
journal, January 2016

  • Zhuang, Zeyan; Shen, Pingchuan; Ding, Siyang
  • Chemical Communications, Vol. 52, Issue 72
  • DOI: 10.1039/C6CC04233C