Conformational change due to intramolecular hydrophobic interaction leads to large blue-shifted emission from single molecular cage solutions

Li, Hui; Xie, Ting-Zheng; Liang, Zihao; Dahal, Dipendra; Shen, Yidan; Sun, Xinyu; Yang, Yuqing; Pang, Yi; Liu, Tianbo

doi:10.1039/c8cc09038f

Title: Conformational change due to intramolecular hydrophobic interaction leads to large blue-shifted emission from single molecular cage solutions

Journal Article · 29 November 2018 · ChemComm

DOI: https://doi.org/10.1039/c8cc09038f · OSTI ID:1608052

^[1];

^[1]; Liang, Zihao ^[1]; Dahal, Dipendra ^[1]; Shen, Yidan ^[1];

^[1]; Yang, Yuqing ^[1];

^[1]; Liu, Tianbo ^[1]

Univ. of Akron, OH (United States)

In this communication, we demonstrate a unique negative solvatochromic emission (NSE) process from a conformational change of a coordination cage in response to solvent composition. The cationic cage contains two tetra-(4-pyridylphenyl)ethylene (TPPE) luminogens on two opposite faces, linked by Pt(PEt₃)₂ and isophthalate. When the solvent changes from acetone/acetonitrile/methanol to water, the emission of single cages gradually shifts to short wavelength (NSE) with a drastic value of ~60 nm. Small angle X-ray scattering (SAXS) measurements indicate a molecular conformational change during the process and intramolecular $$\pi–\pi$$ stacking and hydrophobic interaction between the TPPE planes could be the driving forces. As a comparison, a cage with a longer inter-fluorophore distance does not have such strong intramolecular interactions and only shows regular positive solvatochromic emission (PSE) under the same conditions.

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Research Organization:: Argonne National Laboratory (ANL), Argonne, IL (United States). Advanced Photon Source (APS)

Sponsoring Organization:: National Science Foundation (NSF); USDOE Office of Science (SC)

OSTI ID:: 1608052

Journal Information:: ChemComm, Journal Name: ChemComm Journal Issue: 3 Vol. 55; ISSN 1359-7345

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: ENGLISH

References (46)

Stereoselective Synthesis, Efficient Light Emission, and High Bipolar Charge Mobility of Chiasmatic Luminogens Zhao, Zujin; Lam, Jacky W. Y.; Chan, Carrie Y. K. Advanced Materials, Vol. 23, Issue 45 https://doi.org/10.1002/adma.201102804	journal	October 2011
Anion-Coordination-Induced Turn-On Fluorescence of an Oligourea-Functionalized Tetraphenylethene in a Wide Concentration Range Zhao, Jie; Yang, Dong; Zhao, Yanxia Angewandte Chemie, Vol. 126, Issue 26 https://doi.org/10.1002/ange.201402169	journal	May 2014
A Mechanochromic Single Crystal: Turning Two Color Changes into a Tricolored Switch Ma, Zhiyong; Wang, Zhijian; Meng, Xiao Angewandte Chemie, Vol. 128, Issue 2 https://doi.org/10.1002/ange.201507197	journal	November 2015
Design of Environment-Sensitive Supramolecular Assemblies for Intracellular Drug Delivery: Polymeric Micelles that are Responsive to Intracellular pH Change Bae, Younsoo; Fukushima, Shigeto; Harada, Atsushi Angewandte Chemie International Edition, Vol. 42, Issue 38 https://doi.org/10.1002/anie.200250653	journal	October 2003
Functional Molecular Flasks: New Properties and Reactions within Discrete, Self-Assembled Hosts Yoshizawa, Michito; Klosterman, Jeremy K.; Fujita, Makoto Angewandte Chemie International Edition, Vol. 48, Issue 19, p. 3418-3438 https://doi.org/10.1002/anie.200805340	journal	April 2009
Anion-Coordination-Induced Turn-On Fluorescence of an Oligourea-Functionalized Tetraphenylethene in a Wide Concentration Range Zhao, Jie; Yang, Dong; Zhao, Yanxia Angewandte Chemie International Edition, Vol. 53, Issue 26 https://doi.org/10.1002/anie.201402169	journal	May 2014
A Mechanochromic Single Crystal: Turning Two Color Changes into a Tricolored Switch Ma, Zhiyong; Wang, Zhijian; Meng, Xiao Angewandte Chemie International Edition, Vol. 55, Issue 2 https://doi.org/10.1002/anie.201507197	journal	November 2015
Structural Changes Accompanying Intramolecular Electron Transfer: Focus on Twisted Intramolecular Charge-Transfer States and Structures Grabowski, Zbigniew R.; Rotkiewicz, Krystyna; Rettig, Wolfgang ChemInform, Vol. 34, Issue 52 https://doi.org/10.1002/chin.200352280	journal	December 2003
Photophysical Properties of Organoplatinum(II) Compounds and Derived Self-Assembled Metallacycles and Metallacages: Fluorescence and its Applications Saha, Manik Lal; Yan, Xuzhou; Stang, Peter J. Accounts of Chemical Research, Vol. 49, Issue 11 https://doi.org/10.1021/acs.accounts.6b00416	journal	October 2016
Aggregation-Induced Emission: Together We Shine, United We Soar! Mei, Ju; Leung, Nelson L. C.; Kwok, Ryan T. K. Chemical Reviews, Vol. 115, Issue 21 https://doi.org/10.1021/acs.chemrev.5b00263	journal	October 2015
Self-Assembly of Luminescent Alkynylplatinum(II) Terpyridyl Complexes: Modulation of Photophysical Properties through Aggregation Behavior Wong, Keith Man-Chung; Yam, Vivian Wing-Wah Accounts of Chemical Research, Vol. 44, Issue 6 https://doi.org/10.1021/ar100130j	journal	June 2011
Solvatochromic Dyes as Solvent Polarity Indicators Reichardt, Christian Chemical Reviews, Vol. 94, Issue 8 https://doi.org/10.1021/cr00032a005	journal	December 1994
Supramolecular Coordination: Self-Assembly of Finite Two- and Three-Dimensional Ensembles Chakrabarty, Rajesh; Mukherjee, Partha Sarathi; Stang, Peter J. Chemical Reviews, Vol. 111, Issue 11, p. 6810-6918 https://doi.org/10.1021/cr200077m	journal	November 2011
Fluorescence Lifetime Measurements and Biological Imaging Berezin, Mikhail Y.; Achilefu, Samuel Chemical Reviews, Vol. 110, Issue 5 https://doi.org/10.1021/cr900343z	journal	May 2010
Structural Changes Accompanying Intramolecular Electron Transfer: Focus on Twisted Intramolecular Charge-Transfer States and Structures Grabowski, Zbigniew R.; Rotkiewicz, Krystyna; Rettig, Wolfgang Chemical Reviews, Vol. 103, Issue 10 https://doi.org/10.1021/cr940745l	journal	October 2003
Solvent-Induced Aggregation through Metal···Metal/π···π Interactions: Large Solvatochromism of Luminescent Organoplatinum(II) Terpyridyl Complexes Yam, Vivian Wing-Wah; Wong, Keith Man-Chung; Zhu, Nianyong Journal of the American Chemical Society, Vol. 124, Issue 23 https://doi.org/10.1021/ja025811c	journal	June 2002
Strong Solvatochromic Fluorescence from the Intramolecular Charge-Transfer State Created by Excited-State Intramolecular Proton Transfer Seo, Jangwon; Kim, Sehoon; Park, Soo Young Journal of the American Chemical Society, Vol. 126, Issue 36 https://doi.org/10.1021/ja047815i	journal	September 2004
A Highly Selective Fluorescence Turn-on Sensor for Cysteine/Homocysteine and Its Application in Bioimaging Zhang, Meng; Yu, Mengxiao; Li, Fuyou Journal of the American Chemical Society, Vol. 129, Issue 34 https://doi.org/10.1021/ja073140i	journal	August 2007
Click Synthesis, Aggregation-Induced Emission, E / Z Isomerization, Self-Organization, and Multiple Chromisms of Pure Stereoisomers of a Tetraphenylethene-Cored Luminogen Wang, Jian; Mei, Ju; Hu, Rongrong Journal of the American Chemical Society, Vol. 134, Issue 24 https://doi.org/10.1021/ja208883h	journal	June 2012
Turn-On Fluorescence in Tetraphenylethylene-Based Metal–Organic Frameworks: An Alternative to Aggregation-Induced Emission Shustova, Natalia B.; McCarthy, Brian D.; Dincă, Mircea Journal of the American Chemical Society, Vol. 133, Issue 50 https://doi.org/10.1021/ja209327q	journal	December 2011
Synthesis and Photophysical Properties of a Series of Cyclopenta[ b ]naphthalene Solvatochromic Fluorophores Benedetti, Erica; Kocsis, Laura S.; Brummond, Kay M. Journal of the American Chemical Society, Vol. 134, Issue 30 https://doi.org/10.1021/ja3055029	journal	July 2012
Two-Dimensional Metal–Organic Framework with Wide Channels and Responsive Turn-On Fluorescence for the Chemical Sensing of Volatile Organic Compounds Zhang, Mei; Feng, Guangxue; Song, Zhegang Journal of the American Chemical Society, Vol. 136, Issue 20 https://doi.org/10.1021/ja502643p	journal	May 2014
Highly Emissive Covalent Organic Frameworks Dalapati, Sasanka; Jin, Enquan; Addicoat, Matthew Journal of the American Chemical Society, Vol. 138, Issue 18 https://doi.org/10.1021/jacs.6b02700	journal	April 2016
A Dual-Responsive Bola-Type Supra-amphiphile Constructed from a Water-Soluble Calix[4]pyrrole and a Tetraphenylethene-Containing Pyridine Bis- N -oxide Chi, Xiaodong; Zhang, Huacheng; Vargas-Zúñiga, Gabriela I. Journal of the American Chemical Society, Vol. 138, Issue 18 https://doi.org/10.1021/jacs.6b03159	journal	April 2016
Molecular Face-Rotating Cube with Emergent Chiral and Fluorescence Properties Qu, Hang; Wang, Yu; Li, Zhihao Journal of the American Chemical Society, Vol. 139, Issue 50 https://doi.org/10.1021/jacs.7b07657	journal	September 2017
Fluorescent Metallacage-Core Supramolecular Polymer Gel Formed by Orthogonal Metal Coordination and Host–Guest Interactions Lu, Chenjie; Zhang, Mingming; Tang, Danting Journal of the American Chemical Society, Vol. 140, Issue 24 https://doi.org/10.1021/jacs.8b03781	journal	May 2018
Self-Assembly of Metallacages into Multidimensional Suprastructures with Tunable Emissions Sun, Yan; Yao, Yong; Wang, Heng Journal of the American Chemical Society, Vol. 140, Issue 40 https://doi.org/10.1021/jacs.8b05809	journal	September 2018
Twisted Intramolecular Charge Transfer and Aggregation-Induced Emission of BODIPY Derivatives Hu, Rongrong; Lager, Erik; Aguilar-Aguilar, Angélica The Journal of Physical Chemistry C, Vol. 113, Issue 36 https://doi.org/10.1021/jp902962h	journal	August 2009
Highly emissive platinum(II) metallacages Yan, Xuzhou; Cook, Timothy R.; Wang, Pi Nature Chemistry, Vol. 7, Issue 4 https://doi.org/10.1038/nchem.2201	journal	March 2015
Fluorescent probes for super-resolution imaging in living cells Fernández-Suárez, Marta; Ting, Alice Y. Nature Reviews Molecular Cell Biology, Vol. 9, Issue 12 https://doi.org/10.1038/nrm2531	journal	November 2008
Self-assembly of emissive supramolecular rosettes with increasing complexity using multitopic terpyridine ligands Yin, Guang-Qiang; Wang, Heng; Wang, Xu-Qing Nature Communications, Vol. 9, Issue 1 https://doi.org/10.1038/s41467-018-02959-w	journal	February 2018
Building on architectural principles for three-dimensional metallosupramolecular construction Smulders, Maarten M. J.; Riddell, Imogen A.; Browne, Colm Chem. Soc. Rev., Vol. 42, Issue 4 https://doi.org/10.1039/C2CS35254K	journal	January 2013
Experimental evidence of dual emission in a negatively solvatochromic push–pull pyridinium derivative Carlotti, B.; Cesaretti, A.; Fortuna, C. G. Physical Chemistry Chemical Physics, Vol. 17, Issue 3 https://doi.org/10.1039/C4CP04963B	journal	January 2015
Terpyridine-based metallosupramolecular constructs: tailored monomers to precise 2D-motifs and 3D-metallocages Chakraborty, Sourav; Newkome, George R. Chemical Society Reviews, Vol. 47, Issue 11 https://doi.org/10.1039/C8CS00030A	journal	January 2018
Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole Luo, Jingdong; Xie, Zhiliang; Lam, Jacky W. Y. Chemical Communications, Issue 18 https://doi.org/10.1039/b105159h	journal	January 2001
An aggregation-induced blue shift of emission and the self-assembly of nanoparticles from a novel amphiphilic oligofluorene Zhu, Linna; Yang, Chuluo; Qin, Jingui Chemical Communications, Issue 47 https://doi.org/10.1039/b815431g	journal	January 2008
Aggregation-induced emission: phenomenon, mechanism and applications Hong, Yuning; Lam, Jacky W. Y.; Tang, Ben Zhong Chemical Communications, Issue 29 https://doi.org/10.1039/b904665h	journal	January 2009
Metal-coordination-driven dynamic heteroleptic architectures De, Soumen; Mahata, Kingsuk; Schmittel, Michael Chemical Society Reviews, Vol. 39, Issue 5 https://doi.org/10.1039/b922293f	journal	January 2010
Aggregation-induced emission Hong, Yuning; Lam, Jacky W. Y.; Tang, Ben Zhong Chemical Society Reviews, Vol. 40, Issue 11 https://doi.org/10.1039/c1cs15113d	journal	January 2011
Utilising tetraphenylethene as a dual activator for intramolecular charge transfer and aggregation induced emission Zhang, Guo-Feng; Aldred, Matthew P.; Gong, Wen-Liang Chemical Communications, Vol. 48, Issue 62 https://doi.org/10.1039/c2cc33218c	journal	January 2012
Recent advances in organic mechanofluorochromic materials Chi, Zhenguo; Zhang, Xiqi; Xu, Bingjia Chemical Society Reviews, Vol. 41, Issue 10 https://doi.org/10.1039/c2cs35016e	journal	January 2012
Rethinking the term “pi-stacking” Martinez, Chelsea R.; Iverson, Brent L. Chemical Science, Vol. 3, Issue 7 https://doi.org/10.1039/c2sc20045g	journal	January 2012
Blue fluorescent emitters: design tactics and applications in organic light-emitting diodes Zhu, Minrong; Yang, Chuluo Chemical Society Reviews, Vol. 42, Issue 12 https://doi.org/10.1039/c3cs35440g	journal	January 2013
Reduction and analysis of SANS and USANS data using IGOR Pro Kline, Steven R. Journal of Applied Crystallography, Vol. 39, Issue 6, p. 895-900 https://doi.org/10.1107/S0021889806035059	journal	November 2006
Small-angle scattering. Information content and error analysis Moore, P. B. Journal of Applied Crystallography, Vol. 13, Issue 2 https://doi.org/10.1107/S002188988001179X	journal	April 1980
The Fluorescent Toolbox for Assessing Protein Location and Function Giepmans, B. N. G. Science, Vol. 312, Issue 5771 https://doi.org/10.1126/science.1124618	journal	April 2006

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