Elsevier

Dyes and Pigments

Volume 177, June 2020, 108269
Dyes and Pigments

Multifunctional naphthalene diimide-based coordination polymers: Photochromism and solventchromism

https://doi.org/10.1016/j.dyepig.2020.108269Get rights and content

Highlights

  • Three CPs based on electron-deficient naphthalene diimide dye are prepared.

  • Compounds 1–3 exhibit the visibly detectable photochromism.

  • Compound 1 exhibits solvatochromic behaviour in the presence of different solvents.

  • Solvatochromic effect of compound 1 arise from the intermolecular electron-transfer transition.

Abstract

Naphthalene diimides (NDIs), a class of organic dyes with high photochemical activity and high redox activity, have attracted considerable interest attributing to their photoinduced electron transfer to form stable radical anions upon irradiation in the presence of electron donors. In this study, a naphthalenediimide-based ligand and different aromatic carboxylic acids self-assembled in the presence of zinc ions, forming three novel coordination polymers, [Zn2 (DPMNI) (TPDC)2] (1), [Zn (DPMNI) (BPC)] (2), Zn (DPMNI) (HBTC) (3) (DPMNI = N,N′-bis(4-pyridylmethyl)-1,4,5,8-naphthalene diimide, H2TPDC = thiophene-2,5-dicarboxylic acid, H2BPC = 4,4′-biphenyldicarboxylic acid, H3BTC = 1,3,5-benzenetricarboxylic acid). These coordination polymers characterized by single-crystal X-ray diffraction, elemental analyses, IR spectroscopy, powder X-ray diffraction, and theromgravimetric analysis. Because of the presence of electron-deficient NDI moieties, they exhibit reversible photochromic properties. Furthermore, due to the different π–π interactions between the NDI moieties and aromatic carboxylic acid, compounds 13 exhibit different photosensitive properties. Moreover, the solvatochromic behaviour of compound 1 was also investigated.

Graphical abstract

Three novel NDI-based coordination polymers were prepared by solvothermal reaction, which exhibit reversible photochromic properties and solvatochromic behaviour in the presence of different solvents.

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Introduction

As a class of breakthrough materials, coordination polymers (CPs) have received increasing attention owing to their fascinating structures, designable networks, and various potential applications in catalysis, photoluminescence, chemical sensing, gas storage, and conductivity [1][1], [1](a), [1](b), [1](c), [1](d), [1](e), [1](f), [1](g), [1](h), [1](i). As a new aspect, photochromic CPs have become a hot research topic owing to their well-defined structure and potential application in various fields, such as optical memory, displays, sensors, switches, and erasable copy papers [2][1], [1](a), [1](b), [1](c), [1](d), [1](e), [1](f), [1](g), [1](h), [1](i), [2], [2](a), [2](b), [2](c), [2](d), [2](e), [2](f), [2](g). In general, the photochromic properties of the CPs are derived from either the structural transformation or electron transfer of photoactive organic ligands, in which the photoactive organic ligands can be chemically modified and anchored for their desirable specific properties to the resulting structures [3][3], [3](a), [3](b), [3](c), [3](e), [3](f). However, insight into structure-property relationships and guidance for the rational construction of CPs with adjustable photochromic properties still remains a challenge [4][4], [4](a), [4](b), [4](c), [4](d).

Naphthalenediimide derivatives (NDIs), an attractive class of π-electron-deficient, planar, highly redox-active dye with a substituent on the diimide nitrogen, are often considered as excellent candidates for the construction of photochromic CPs, as they can undergo single one-electron reduction forming colored organic radicals [5][5], [5](a), [5](b), [5](c), [5](d), [5](e), [5](f), [5](g), [5](h). NDI-based ligands with pyridyl substituent have multiple potential coordination sites, including terminal O and N atoms. This diverse coordination mode between the NDIs ligand and metal cations not only provides more opportunities for constructing various network structures, but also adjusts the photochromic properties of the resulting CPs [6][6], [6](a), [6](b), [6](c), [6](d). Up to now, much research has been made on designing and synthesizing the NDI-based compounds, exhibiting interesting luminescence and catalysis [7][7], [7](a), [7](b), [7](c), [7](d), [7](e), [7](f). There have been several examples involving NDI-based CPs reported, but their photochromic properties have rarely been investigated [[8], [8](a), [8](b), [8](c)]. Especially, almost no solvatochromic behaviour of NDI-based CPs has been reported.

Inspired from the crystal engineering and photochromic mechanism of electron-transfer CPs, we envisaged that it should be suitable to select electron-deficient NDIs as the organic ligands and electron-rich aromatic carboxylic acids as the secondary building linkers to construct photochromic CPs, and then further study the effect of secondary building unit on the photochromic properties of CPs. Hence, an NDI derivative- N,N′-bis(4-pyridylmethyl)-1,4,5,8-naphthalene diimide (DPMNI) and three different aromatic carboxylic acids were selected to construct three coordination polymers [Zn2 (DPMNI) (TPDC)2] (1), [Zn (DPMNI) (BPC)] (2), Zn (DPMNI) (HBTC) (3) (H2TPDC = thiophene-2,5-dicarboxylic acid, H2BPC = 4,4′-biphenyldicarboxylic acid, H3BTC = 1,3,5-benzenetricarboxylic acid, Schemes S1–S3). Compounds 13 all exhibit photochromism after irradiation with a Xe lamp and the resulting photoproducts were stable for several days. Notably, the different aromatic carboxylic acid linkers formed divergent supramolecular interactions (π–π and lone pair–π interactions), and thus significantly affected the structures and photochromic properties. The crystal structures, photochromism, and solvatochromism of these compounds, will be represented and discussed in this study.

Section snippets

Materials and measurements

All chemicals were purchased from commercial sources and used without further purification. Thermogravimetric analysis (TGA) was carried out using a Mettler Toledo TGA2 system analyzer under nitrogen atmosphere from 30 °C to 800 °C at a ramp rate of 10 °C/min. Elemental analyses (C, H and N) were carried out using a PerkinElmer 240C elemental analyzer. Powder X-ray diffraction (PXRD) patterns were recorded using a Rigaku Ultima IV diffractometer equipped with Cu Kα (λ = 1.5418 Å) radiation.

Results and discussions

Single-crystal X-ray diffraction analysis shows that compound 1 crystallizes in the monoclinic space group C2/c, and the asymmetric unit consists of a crystallographically independent Zn cation, one TPDC2− ligand, and one half of DPMNI ligand. As shown in Fig. 1a, the geometry at the Zn center is a distorted tetrahedron formed by three O atoms from three TPDC2− ligands with Zn–O distances of 1.952 (3)–1.997 (3) Å and one N atom from the DPMNI ligand with Zn–N distance of 2.012 (3) Å. The

Conclusion

In summary, three photochromic coordination polymers assembled from a NDI related ligand and different aromatic carboxylic acids were prepared and characterized. Interestingly, these three coordination polymers exhibit reversible photochromic properties upon irradiation in the solid state. Due to different π–π interactions between the NDI core and aromatic carboxylic acid, compounds 13 exhibit different photosensitive properties. Furthermore, compound 1 exhibits reversible solvatochromic

CRediT authorship contribution statement

Jian-Jun Liu: Writing - review & editing. Shu-Biao Xia: Writing - review & editing. Dan Liu: Writing - review & editing. Juying Hou: Writing - review & editing. Hongbo Suo: Writing - review & editing. Fei-Xiang Cheng: Writing - review & editing.

Declaration of competing interest

None.

Acknowledgements

This work has been supported by National Natural Science Foundation of China (21961030, and 51764048), Yunnan Province Thousand Youth Talents Plan, Program of Innovative Research Team (in science and technology) in University of Yunnan Province, and Application Basis Research Project of Yunnan Province Science and Technology Department (award No. 2017FD144).

References (18)

  • S.J. Liu et al.

    In-situ synthesis of molecular magnetorefrigerant materials

    Coord Chem Rev

    (2019)
    J. Lee et al.

    Metal–organic framework materials as catalysts

    Chem Soc Rev

    (2009)
    T.F. Zheng et al.

    Two GdIII complexes with different structures and magnetocaloric properties induced by metal ion sources

    New J Chem

    (2019)
    W. Lu et al.

    Tuning the structure and function of metal–organic frameworks via linker design

    Chem Soc Rev

    (2014)
    I. Nath et al.

    Metal organic frameworks mimicking natural enzymes: a structural and functional analogy

    Chem Soc Rev

    (2016)
    M. Pan et al.

    Epitaxial growth of hetero-Ln-MOF hierarchical single crystals for domain- and orientation-controlled multicolor luminescence 3D coding capability

    Angew Chem Int Ed

    (2017)
    J. Jiang et al.

    Brønsted acidity in metal–organic frameworks

    Chem Rev

    (2015)
    S.L. Yao et al.

    A ZnII-based Metal−Organic framework with a rare tcj topology as a turn-on fluorescent sensor for acetylacetone

    Inorg Chem

    (2019)
    S.J. Liu et al.

    Temperature- and vapor-induced reversible single-crystal-to-single-crystal transformations of three 2D/3D GdIII-organic frameworks exhibiting significant magnetocaloric effects

    Dalton Trans

    (2017)
  • A. Fihey et al.

    Multiphotochromic molecular systems

    Chem Soc Rev

    (2015)
    Q. Shi et al.

    Three viologen-derived Zn-organic materials: photochromism, photomodulated fluorescence, and inkless and erasable prints

    Dalton Trans

    (2019)
    H. Dong et al.

    Organic photoresponse materials and devices

    Chem Soc Rev

    (2012)
    X. Kuang et al.

    Supramolecular aggregation of a redox-active copper-naphthalenediimide network with intrinsic electron conduction

    Chem Commun

    (2019)
    Y.B. Su et al.

    Energy-dependent photochromism at room temperature for visually detecting and distinguishing X-rays

    Chem Commun

    (2018)
    M. Irie et al.

    Photochromism of diarylethene molecules and crystals: memories, switches, and actuators

    Chem Rev

    (2014)
    S. Takami et al.

    Photochromism of mixed crystals containing bisthienyl-, bisthiazolyl-, and bisoxazolylethene derivatives

    J Am Chem Soc

    (2007)
  • M.Q. Zhu et al.

    Spiropyran-based photochromic polymer nanoparticles with optically switchable luminescence

    J Am Chem Soc

    (2006)
    E. Hadjoudis et al.

    Photochromism and thermochromism of Schiff bases in the solid state: structural aspects

    Chem Soc Rev

    (2004)
    F.Y. Lin et al.

    Multiple pathways for the primary step of the spiropyran photochromic reaction: a CASPT2//CASSCF study

    J Am Chem Soc

    (2013)
    R. Lyndon et al.

    Dynamic photo-switching in metal–organic frameworks as a route to low-energy carbon dioxide capture and release

    Angew Chem Int Ed

    (2013)
    J. Liu

    Three 1D coordination polymers based on bipyridinium carboxylate ligands: Photochromism

    Dyes Pigments

    (2019)
  • H.L. Xu et al.

    The impact of metal ions on photoinduced electron-transfer properties: four photochromic metal–organic frameworks based on a naphthalenediimide chromophore

    CrystEngComm

    (2018)
    J.J. Liu et al.

    Anion-controlled architecture and photochromism of naphthalene diimide-based coordination polymers

    Polymers

    (2018)
    X.Y. Lv et al.

    Photochromic metal complexes of N-Methyl-4,4′-Bipyridinium: mechanism and influence of halogen atoms

    Inorg Chem

    (2012)
    S.J. Liu et al.

    High proton conduction in two CoII and MnII anionic metal–organic frameworks derived from 1,3,5-benzenetricarboxylic acid

    Cryst Growth Des

    (2016)
  • S.V. Bhosale et al.

    Chemistry of naphthalene diimides

    Chem Soc Rev

    (2008)
    R.E. Dawson et al.

    Experimental evidence for the functional relevance of anion–π interactions

    Nat Chem

    (2010)
    C.R. Wade et al.

    Facile deposition of multicolored electrochromic metal–organic framework thin films

    Angew Chem Int Ed

    (2013)
    L. Qu et al.

    Porous molecular conductor: electrochemical fabrication of through-space conduction pathways among linear coordination polymers

    J Am Chem Soc

    (2019)
    M.A. Kobaisi et al.

    Functional naphthalene diimides: synthesis, properties, and applications

    Chem Rev

    (2016)
    S. Goswami et al.

    Photoexcited naphthalene diimide radical anion linking the nodes of a Metal−Organic framework: a heterogeneous super-reductant

    Chem Mater

    (2018)
    L. Qin et al.

    A naphthalenediimide-based Co-MOF as naked-eye colorimetric sensor to humidity

    J Solid State Chem

    (2019)
    M.K. Wu et al.

    An ultrastable metal–organic framework with open coordinated sites realizing selective separation toward cationic dyes in aqueous solution

    Cryst Growth Des

    (2017)
  • M. Pan et al.

    Progress in the study of metal–organic materials applying naphthalene diimide (NDI) ligands

    Coord Chem Rev

    (2011)
    C.F. Leong et al.

    Controlling charge separation in a novel donor–acceptor metal–organic framework via redox modulation

    Chem Sci

    (2014)
    C. Fu et al.

    The influence of the secondary building linker geometry on the photochromism of naphthalenediimide-based metal–organic frameworks

    CrystEngComm

    (2018)
    J.Z. Liao et al.

    Exceptional photosensitivity of a polyoxometalate-based charge-transfer hybrid material

    Chem Commun

    (2016)
  • N. Sakai et al.

    Core-substituted naphthalenediimides

    Chem Commun

    (2010)
    Y. Zhao et al.

    Catalysis with anion-π interactions

    Angew Chem Int Ed

    (2013)
    Y. Zhao et al.

    Enolate chemistry with anion–π interactions

    Nat Commun

    (2014)
    L. Liu et al.

    Anion-π catalysis of diels-alder reactions

    Angew Chem Int Ed

    (2017)
    J.Z. Liao et al.

    Multifunctional radical-doped polyoxometalate-based Host−Guest material: photochromism and photocatalytic activity

    Inorg Chem

    (2015)
    T. Ono et al.

    Multicomponent molecular puzzles for photofunction design: emission color variation in lewis Acid−Base pair crystals coupled with guest-to-host charge transfer excitation

    J Am Chem Soc

    (2015)
  • Z. Li et al.

    Photochromic naphthalene diimide Cd-MOFs based on different second dicarboxylic acid ligands

    CrystEngComm

    (2018)
    Y. Zhou et al.

    A bifunctional anionic Metal−Organic framework: reversible photochromism and selective adsorption of methylene blue

    Cryst Growth Des

    (2018)
    Y.X. Xie et al.

    A naphthalenediimide-based Metal−Organic framework and thin film exhibiting photochromic and electrochromic properties

    Inorg Chem

    (2016)
  • G. Koshkakaryan et al.

    Alternative Donor−Acceptor stacks from crown ethers and naphthalene diimide derivatives: rapid, selective formation from solution and solid state grinding

    J Am Chem Soc

    (2009)
There are more references available in the full text version of this article.

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