Two-photon excited deep-red and near-infrared emissive organic co-crystals

Yu Wang; Huang Wu; Penghao Li; Su Chen; Leighton O. Jones; Martín A. Mosquera; Long Zhang; Kang Cai; Hongliang Chen; Xiao Yang Chen; Charlotte L. Stern; Michael R. Wasielewski; Mark A. Ratner; George C. Schatz; J. Fraser Stoddart

doi:10.1038/s41467-020-18431-7

Two-photon excited deep-red and near-infrared emissive organic co-crystals

Yu Wang, Huang Wu, Penghao Li, Su Chen, Leighton O. Jones, Martín A. Mosquera, Long Zhang, Kang Cai, Hongliang Chen, Xiao Yang Chen, Charlotte L. Stern, Michael R. Wasielewski, Mark A. Ratner, George C. Schatz, J. Fraser Stoddart^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

98 Scopus citations

Abstract

Two-photon excited near-infrared fluorescence materials have garnered considerable attention because of their superior optical penetration, higher spatial resolution, and lower optical scattering compared with other optical materials. Herein, a convenient and efficient supramolecular approach is used to synthesize a two-photon excited near-infrared emissive co-crystalline material. A naphthalenediimide-based triangular macrocycle and coronene form selectively two co-crystals. The triangle-shaped co-crystal emits deep-red fluorescence, while the quadrangle-shaped co-crystal displays deep-red and near-infrared emission centered on 668 nm, which represents a 162 nm red-shift compared with its precursors. Benefiting from intermolecular charge transfer interactions, the two co-crystals possess higher calculated two-photon absorption cross-sections than those of their individual constituents. Their two-photon absorption bands reach into the NIR-II region of the electromagnetic spectrum. The quadrangle-shaped co-crystal constitutes a unique material that exhibits two-photon absorption and near-infrared emission simultaneously. This co-crystallization strategy holds considerable promise for the future design and synthesis of more advanced optical materials.

Original language	English (US)
Article number	4633
Journal	Nature communications
Volume	11
Issue number	1
DOIs	https://doi.org/10.1038/s41467-020-18431-7
State	Published - Dec 1 2020

Funding

The authors thank Northwestern University (NU) for its support of this research. The authors would like to thank Professor Justin Notestein and Mark Taylor for technical support on solid-state UV-Vis absorption spectroscopy measurements. The A1R-MP+ multiphoton microscope was acquired through an S10 shared instrumentation grant awarded to Teng-Leong Chew (1 S10 OD010398-01). This work made use of the NUFAB facility of Northwestern University’s NUANCE Center, NNCI-SHyNE Resource (NSF ECCS-1542205) and the MRSEC program (NSF DMR-1720139) at the Materials Research Center. L.O.J. and G.C.S. acknowledge support from NSF grant CHE-1836392 (two-photon applications); M.A.M., G.C.S., and M.A.R. acknowledge support from the Department of Energy, grant DE-AC02-06CH11357 (functional materials and spectroscopy applications), and grant DE-SC0004752 (theory development). This research was also supported in part through the computational resources and staff contributions provided for the Quest high performance computing facility at Northwestern University which is jointly supported by the Office of the Provost, the Office for Research, and Northwestern University Information Technology. S.C. and M.R.W. thank the support from the U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences under Award DE-FG02-99ER14999.

ASJC Scopus subject areas

General
General Physics and Astronomy
General Chemistry
General Biochemistry, Genetics and Molecular Biology

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10.1038/s41467-020-18431-7

Cite this

@article{bb6a66c147e84eb2a1db088fa29cbd2a,

title = "Two-photon excited deep-red and near-infrared emissive organic co-crystals",

abstract = "Two-photon excited near-infrared fluorescence materials have garnered considerable attention because of their superior optical penetration, higher spatial resolution, and lower optical scattering compared with other optical materials. Herein, a convenient and efficient supramolecular approach is used to synthesize a two-photon excited near-infrared emissive co-crystalline material. A naphthalenediimide-based triangular macrocycle and coronene form selectively two co-crystals. The triangle-shaped co-crystal emits deep-red fluorescence, while the quadrangle-shaped co-crystal displays deep-red and near-infrared emission centered on 668 nm, which represents a 162 nm red-shift compared with its precursors. Benefiting from intermolecular charge transfer interactions, the two co-crystals possess higher calculated two-photon absorption cross-sections than those of their individual constituents. Their two-photon absorption bands reach into the NIR-II region of the electromagnetic spectrum. The quadrangle-shaped co-crystal constitutes a unique material that exhibits two-photon absorption and near-infrared emission simultaneously. This co-crystallization strategy holds considerable promise for the future design and synthesis of more advanced optical materials.",

author = "Yu Wang and Huang Wu and Penghao Li and Su Chen and Jones, {Leighton O.} and Mosquera, {Mart{\'i}n A.} and Long Zhang and Kang Cai and Hongliang Chen and Chen, {Xiao Yang} and Stern, {Charlotte L.} and Wasielewski, {Michael R.} and Ratner, {Mark A.} and Schatz, {George C.} and Stoddart, {J. Fraser}",

note = "Funding Information: The authors thank Northwestern University (NU) for its support of this research. The authors would like to thank Professor Justin Notestein and Mark Taylor for technical support on solid-state UV-Vis absorption spectroscopy measurements. The A1R-MP+ multiphoton microscope was acquired through an S10 shared instrumentation grant awarded to Teng-Leong Chew (1 S10 OD010398-01). This work made use of the NUFAB facility of Northwestern University{\textquoteright}s NUANCE Center, NNCI-SHyNE Resource (NSF ECCS-1542205) and the MRSEC program (NSF DMR-1720139) at the Materials Research Center. L.O.J. and G.C.S. acknowledge support from NSF grant CHE-1836392 (two-photon applications); M.A.M., G.C.S., and M.A.R. acknowledge support from the Department of Energy, grant DE-AC02-06CH11357 (functional materials and spectroscopy applications), and grant DE-SC0004752 (theory development). This research was also supported in part through the computational resources and staff contributions provided for the Quest high performance computing facility at Northwestern University which is jointly supported by the Office of the Provost, the Office for Research, and Northwestern University Information Technology. S.C. and M.R.W. thank the support from the U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences under Award DE-FG02-99ER14999. Publisher Copyright: {\textcopyright} 2020, The Author(s).",

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doi = "10.1038/s41467-020-18431-7",

language = "English (US)",

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T1 - Two-photon excited deep-red and near-infrared emissive organic co-crystals

AU - Wang, Yu

AU - Wu, Huang

AU - Li, Penghao

AU - Chen, Su

AU - Jones, Leighton O.

AU - Mosquera, Martín A.

AU - Zhang, Long

AU - Cai, Kang

AU - Chen, Hongliang

AU - Chen, Xiao Yang

AU - Stern, Charlotte L.

AU - Wasielewski, Michael R.

AU - Ratner, Mark A.

AU - Schatz, George C.

AU - Stoddart, J. Fraser

N1 - Funding Information: The authors thank Northwestern University (NU) for its support of this research. The authors would like to thank Professor Justin Notestein and Mark Taylor for technical support on solid-state UV-Vis absorption spectroscopy measurements. The A1R-MP+ multiphoton microscope was acquired through an S10 shared instrumentation grant awarded to Teng-Leong Chew (1 S10 OD010398-01). This work made use of the NUFAB facility of Northwestern University’s NUANCE Center, NNCI-SHyNE Resource (NSF ECCS-1542205) and the MRSEC program (NSF DMR-1720139) at the Materials Research Center. L.O.J. and G.C.S. acknowledge support from NSF grant CHE-1836392 (two-photon applications); M.A.M., G.C.S., and M.A.R. acknowledge support from the Department of Energy, grant DE-AC02-06CH11357 (functional materials and spectroscopy applications), and grant DE-SC0004752 (theory development). This research was also supported in part through the computational resources and staff contributions provided for the Quest high performance computing facility at Northwestern University which is jointly supported by the Office of the Provost, the Office for Research, and Northwestern University Information Technology. S.C. and M.R.W. thank the support from the U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences under Award DE-FG02-99ER14999. Publisher Copyright: © 2020, The Author(s).

PY - 2020/12/1

Y1 - 2020/12/1

N2 - Two-photon excited near-infrared fluorescence materials have garnered considerable attention because of their superior optical penetration, higher spatial resolution, and lower optical scattering compared with other optical materials. Herein, a convenient and efficient supramolecular approach is used to synthesize a two-photon excited near-infrared emissive co-crystalline material. A naphthalenediimide-based triangular macrocycle and coronene form selectively two co-crystals. The triangle-shaped co-crystal emits deep-red fluorescence, while the quadrangle-shaped co-crystal displays deep-red and near-infrared emission centered on 668 nm, which represents a 162 nm red-shift compared with its precursors. Benefiting from intermolecular charge transfer interactions, the two co-crystals possess higher calculated two-photon absorption cross-sections than those of their individual constituents. Their two-photon absorption bands reach into the NIR-II region of the electromagnetic spectrum. The quadrangle-shaped co-crystal constitutes a unique material that exhibits two-photon absorption and near-infrared emission simultaneously. This co-crystallization strategy holds considerable promise for the future design and synthesis of more advanced optical materials.

AB - Two-photon excited near-infrared fluorescence materials have garnered considerable attention because of their superior optical penetration, higher spatial resolution, and lower optical scattering compared with other optical materials. Herein, a convenient and efficient supramolecular approach is used to synthesize a two-photon excited near-infrared emissive co-crystalline material. A naphthalenediimide-based triangular macrocycle and coronene form selectively two co-crystals. The triangle-shaped co-crystal emits deep-red fluorescence, while the quadrangle-shaped co-crystal displays deep-red and near-infrared emission centered on 668 nm, which represents a 162 nm red-shift compared with its precursors. Benefiting from intermolecular charge transfer interactions, the two co-crystals possess higher calculated two-photon absorption cross-sections than those of their individual constituents. Their two-photon absorption bands reach into the NIR-II region of the electromagnetic spectrum. The quadrangle-shaped co-crystal constitutes a unique material that exhibits two-photon absorption and near-infrared emission simultaneously. This co-crystallization strategy holds considerable promise for the future design and synthesis of more advanced optical materials.

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Two-photon excited deep-red and near-infrared emissive organic co-crystals

Abstract

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CCDC 2004160: Experimental Crystal Structure Determination

CCDC 2004158: Experimental Crystal Structure Determination

CCDC 2004159: Experimental Crystal Structure Determination

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Two-photon excited deep-red and near-infrared emissive organic co-crystals

Abstract

Funding

ASJC Scopus subject areas

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Datasets

CCDC 2004160: Experimental Crystal Structure Determination

CCDC 2004158: Experimental Crystal Structure Determination

CCDC 2004159: Experimental Crystal Structure Determination

Cite this