Control of Aggregation-Induced Emission from a Tetraphenylethene

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Control of Aggregation-Induced Emission from a Tetraphenylethene Derivative through the Components in the Co-Crystal Takahiro Jimbo, Mikako Tsuji, Ryosuke Taniguchi, Kazuki Sada, and Kenta Kokado Cryst. Growth Des., Just Accepted Manuscript • DOI: 10.1021/acs.cgd.8b00141 • Publication Date (Web): 01 Jun 2018 Downloaded from http://pubs.acs.org on June 1, 2018

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Crystal Growth & Design

Control of Aggregation-Induced Emission from a Tetraphenylethene

Derivative

through

the

Components in the Co-Crystal Takahiro Jimbo,† Mikako Tsuji,† Ryosuke Taniguchi,‡ Kazuki Sada,†,‡,* and Kenta Kokado†,‡,* †

Graduate School of Chemical Sciences and Engineering, Hokkaido University, Kita10 Nishi8,

Kita-ku, Sapporo, 060-0810, Japan. ‡

Faculty of Science, Hokkaido University, Kita10 Nishi8, Kita-ku, Sapporo, 060-0810, Japan.

ACS Paragon Plus Environment

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Abstract

We aim to control the photoluminescence property of co-crystals derived from an aggregationinduced emission luminogen (AIEgen) through other components in the co-crystal. For this purpose, we prepared the co-crystal of a typical AIEgen, tetraphenylethene having four hydroxy groups (THPE), and hydrogen bond acceptors (HBAs) containing nitrogen atoms. From the crystallographic study, the hydrogen bonding pattern or inclusion of crystallization solvents are significantly influenced by the employed HBA, depending on the size, position of nitrogen atoms, or basicity of the HBA, thanks to the moderate hydrogen bonding ability of THPE. The photoluminescence properties of the co-crystals are governed by the employed HBA, thus cocrystals derived from imidazole derivatives or 1,4-diazabicyclo[2.2.2]octane (DABCO) exhibit intense photoluminescence, while those from pyridine derivatives and an electron-deficient imidazole derivative do not show any photoluminescence. The involvement of photo-induced electron transfer (PET) causes quenching of the co-crystals derived from pyridine derivatives, which is confirmed by theoretical computations. These observations imply that the photoluminescence properties of co-crystals derived from AIEgen can be tuned through other components in the co-crystal.


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Introduction Aggregation-induced emission (AIE) is an emerging photoluminescence phenomenon in the field of materials chemistry, in which an AIE luminogen (AIEgen) shows intense photoluminescence in its aggregated or solid states but only weak or no emission in its solution state.1–4 AIEgens have been developed as a new class of optical and luminescent materials because of their attractive switching property, following the definition of AIE by Tang et al. in 2001.5 A number of studies on AIEgens have been presented to date, which have resulted in their feasible applications in optoelectronics,6,7 and as fluorescent probes8,9 and biosensors.10,11 Tetraphenylethene (TPE) is a typical AIEgen, and its derivatives have been frequently used as a source of various AIEgens.1,2 Within the AIE research community, the restriction of intramolecular rotation (RIR) of the phenyl rings, that is, the restriction of thermal perturbations, is generally believed to be the main reason for the quenching of TPE derivatives in the solution state. We recently proved that a π twist of the central C=C bond of TPE was in fact responsible for the quenching in the solution state.12 The π twist of TPE has historically been disclosed through transient spectroscopy,13–16 as well as the cooling- and viscosity-induced luminescence enhancement of stilbene derivatives.17–19 The π twist of TPE can convincingly explain the results from several studies that have focused on the emissive events of TPE derivatives through supra-molecular interactions, and thus not through aggregation .20–23 For instance, Shinkai and co-workers presented “cyclization-induced emission” of a TPE derivative with zinc dipicolylamine groups interacting with dicarboxylic acids in an homogeneous buffer solution.20 Hahn and co-workers recently reported the emission of an N-heterocyclic carbene (NHC)-tethering TPE derivative through metal complexation of the NHC moiety.23 Additionally, we have demonstrated emission control of TPE derivatives through


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a supramolecular interaction, by incorporation in network polymers or liquefaction.24-29 These facts validate the idea that aggregate formation is just one way to cause AIE. As a novel matrix to control the photoluminescence of TPE derivatives, we herein focus on the use of co-crystals. Various co-crystal systems to control the photoluminescence of the components have been reported, which have used π-π stacking, energy transfer, or charge transfer.30–38 Indeed, co-crystals can provide a sufficiently rigid matrix to suppress the π twist of TPE derivatives, as evidenced by the example of liquefaction.29 TPE derivatives having carboxylic acid groups39–42 or pyridyl groups43–46 have been employed as organic ligands of luminescent metal–organic frameworks (MOFs), which have been applied in sensors or lasers. Although, for pure organic co-crystals of TPE derivatives, the employment of hydrogen bonds or halogen bonds have been reported,47,48 their photoluminescence properties remain unclear. In this study, we selected tetra(4-hydroxyphenyl)ethene (THPE) as the platform AIEgen, and prepared hydrogen-bonding based co-crystals from THPE and various hydrogen bond acceptors (HBAs), which were cyclic compounds containing nitrogen atoms.


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Experimental Section Materials and Measurements. THPE49 and HBA 750 were prepared according to the reported procedure. Other reagents and solvents were purchased from commercial sources, and used without further purification. 1HNMR spectra were measured on a Bruker DRX-500MHz spectrometer, using 0.05% tetramethylsilane (TMS) as an internal standard. Photoluminescence spectra were obtained with a Shimadzu RF5300PC spectrofluorometer. The absolute photoluminescence quantum yield (ΦF) was measured by a Hamamatsu C9920-02 absolute photoluminescence quantum yield measurement system equipped with an integrating sphere apparatus and a 150 W continuouswave xenon light source. X-ray Crystallography Analysis Single-crystals were mounted in the loop using paraffin oil. The data were collected on a Rigaku R-AXIS RAPID diffractometer with graphite monochromated Mo Kα radiation (λ = 0.71069 Å) and a rotating-anode generator operating at 50 kV and 40 mA, and on a Rigaku XtaLAB Synergy-S with graphite monochromated Cu Kα radiation (λ = 1.5418 Å) and a PhotonJet-S microfocus generator operating at 50 kV and 1 mA. Diffraction data were collected and processed using the CrystalClear51 and CrysAlisPro program, respectively. Structures were solved by direct methods using SHELXS-97.52 Structural refinements were conducted by the full-matrix least-squares method using SHELXH-97. Non-H atoms were refined anisotropically, and H atoms were refined using a riding model. All calculations were performed using the Yadokari-XG53 and the OLEX² software packages.


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Preparation of co-crystals of THPE and HBAs 1-6 and 8-15. THPE (40 mg, 0.1 mmol) and 2 eq. of HBA (2-6, 8-15) or 4 eq. of HBA (1) were dissolved in the crystalizing solvents shown in Table 1, and the solvent was slowly evaporated under ambient conditions to produce single co-crystals. Preparation of co-crystal THPE–7. HBA 7 (35 mg, 0.078 mmol) was dissolved in chloroform (30 mL), and the solution was filtered. One milliliter of an acetonitrile solution of THPE (10 mg, 0.025 mmol) was slowly placed on the filtrate (9 mL), and left to stand to obtain the single co-crystal.


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Results and Discussion

Figure 1. Preparation of co-crystals from THPE as a hydrogen bond donor and nitrogen containing cyclic molecules (1-15) as hydrogen bond acceptors.

THPE was selected as the AIE-active hydrogen bond donor for the preparation of co-crystals (Figure 1), which was known to form various inclusion crystals.54 As the HBA, 14 cyclic molecules containing nitrogen atoms were employed. The co-crystals were prepared by slow evaporation of solvent from a mixed solution of THPE and each HBA with an equivalent amount of hydroxy groups and nitrogen atoms (THPE/HBA = 1/2 for 2–6 and 8–15, THPE/1 = 1/4), except for HBA 7 (THPE/7 = 1/3).


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Table 1. Results of crystallization of THPE and HBAs. THPE/HBAa

HBA Crystalizing solvent

HB patternb

Included solvent (THPE/solvent)

1

EtOAc

1/2

A

–

2

MeOH/H2O (4/1)

1/2

A

–

3

MeOH/H2O (2/1)

1/1

B

–

Acetone

1/2

D

Acetone (1/1)

EtOAc

2/3

D

EtOAc (2/1), H2O (1/1)

MeOH

1/1

D

MeOH (1/4)

MeOH/H2O (4/1)

1/2

A

–

MeOH

1/1

D

MeOH (1/4)

5

EtOAc

1/2

A

–

6

EtOAc/MeOH (3/2)

2/3

D

EtOAc (1/1.5)

7

MeCN/CHCl3

1/1

D

CHCl3 (1/3)

8

EtOAc/MeOH (3/2)

1/2

D

–

9

EtOAc

1/2

C

–

MeCN

1/2

B

MeCN (1/1)

10

EtOAc/MeOH (3/1)

1/2

B

–

11

Acetone

1/2

C

–

MeOH

1/2

C

–

12

Acetone/Toluene (1/1)

1/2

B

–

13

EtOAc/Toluene (2/1)

1/2

B

Toluene (1/2)

EtOAc/p-Xylene (2/1)

1/2

B

p-Xylene (1/2)

EtOAc/Bromobenzene (2/1)

1/2

B

Bromobenzene (1/2)

14

EtOAc/MeOH (2/1)

1/3

B

EtOAc (1/2)

15

Acetone/Toluene (4/1)

1/2

B

–

4

a

Confirmed by X-ray crystallography and 1H NMR spectroscopy. b Hydrogen bonding pattern.


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Figure 2. (a) The hydrogen bonding patterns (type A–D) of the co-crystals, and crystal structures of (b) THPE–1, (c) THPE–3, (d) THPE–9, and (d) THPE–8 and (See more in Figure S1).

THPE formed good quality co-crystals with all employed HBAs, which were suitable for Xray crystallography analysis (Figures 2 and S1). We classified hydrogen bonding pattern in these co-crystals as types A–D, as shown in Figure 2a. Types A–C contain a one-dimensional THPE tape, while type D contains an isolated THPE surrounded by HBA. Among types A–C, type A forms a one-dimensional tape through two hydrogen bonds by donating two hydrogen atoms from two of the hydroxy groups. The redundant two hydrogen atoms are involved in a second hydrogen bond with HBA, and an inter-tape hydrogen bond is not detected. In type B, all HBAs on the same side of the THPE one-dimensional tape form hydrogen bonds with the other onedimensional tape of THPE, which accordingly create a two-dimensional sheet. Type C is similar to type B, but the HBAs are on the same side of THPE so the one-dimensional tape forms


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hydrogen bonds not only with one tape of THPE but also with another tape of THPE, hence a three-dimensional network structure is formed. For pyridine derivatives (1–7), THPE formed hydrogen bonds between the hydroxy group and the nitrogen atom of the pyridine group. Each pyridine group was not converted to a protonated pyridinium cation, as was evidenced from the intra-annular C-N-C angles of ~116º, which is typical for neutral pyridines.55,56 Figure 2b shows the crystal structure of co-crystal THPE–1. The crystal analysis and 1H NMR spectroscopy after digestion of the co-crystal confirmed the 1/2 ratio of THPE/1. The crystal of THPE–2 exhibited type A hydrogen bonding pattern as same as THPE–1. The co-crystals with HBAs with chelating ability, such as 4 and 5 (THPE–4 and THPE–5) also exhibited the same hydrogen bonding pattern, as was observed from X-ray crystallography and 1H NMR spectroscopy. For the HBAs having nitrogen atoms at the opposite ends, such as 3, THPE formed a different type of hydrogen bonding pattern from type A, as shown as type B in Figure 2a, in which the one-dimensional tape of THPE was crosslinked by 3 (Figure 2c). With the larger HBAs, such as 6 and 7, THPE could not form the one-dimensional tape, and all the hydrogen atoms of THPE were used for hydrogen bonding with HBA, which was classified as type D in Figure 2a. The oxygen atoms of the imide moiety in HBA 7 also accepted a hydrogen bond. Additionally, cocrystals THPE–6 and THPE–7 included the crystallization solvents as described in Table 1. The co-crystals THPE–3 and THPE–4 could also include the crystallization solvents, upon changing the hydrogen bonding patterns to type D. For examples, the hydroxy groups in THPE–3 formed hydrogen bonds of THPE with 3 in the case of acetone as the crystallization solvent, with H2O in the case of ethyl acetate and H2O as the crystallization solvent, and with methanol in the case of methanol as the crystallization solvent. HBA 8 also formed a co-crystal (THPE–8) having a


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type D hydrogen bonding pattern, presumably because of the higher basicity of the tertiary amine (Figure 2e). For imidazole derivatives (9– –15), THPE formed a hydrogen bond between a hydroxy group and the nitrogen atom of an imidazole group. Each imidazole was not converted to a protonated imidazolium cation, as was evidenced from the intra-annular C=N-C angles of 103~106º with 2~3º smaller than C-N-C angles in the same imidazolium ring, which is largely different from an imidazolium cation.57,58 As with the case of HBA 3, a type B hydrogen bonding pattern was observed for THPE–10, THPE–12, and THPE–15. However, the co-crystals THPE–9 and THPE–11 formed a type C hydrogen bonding pattern (Figure 2d). The co-crystals THPE–13 and THPE–14 included the crystallization solvents, as shown in Table 1, and formed with a type B hydrogen bonding pattern. The included solvents were not involved in the hydrogen bonds of the co-crystals. Additionally, the bulky HBA 14 partially formed a dyad, thus the ratio of THPE/14 became 1/3. In all cases of imidazole HBAs, the one-dimensional tape of THPE was formed, probably owing to the properties of the imidazole, such as the short distance between the two nitrogen atoms, the opposite positions of the nitrogen atoms, and the moderate basicity.


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Figure 3. (a) Photographs of THPE and its co-crystals under room light and UV (365 nm) irradiation. The solvent in parentheses shows the included solvent. (b) Photoluminescence spectra of THPE and its co-crystals (λex = 350 nm). The photoluminescence properties of the obtained co-crystals were investigated. THPE originally exhibited an intense emission at around 440 nm in the solid state, which was derived from its AIE character, as shown in Figure 3. However, co-crystals of THPE with HBAs of pyridine derivatives (1–7) did not exhibit any photoluminescence, as shown in Figure 3a. Furthermore, the co-crystals of THPE with the HBAs of imidazole derivatives (8–14) and tertiary amine (7) exhibited an intense emission at around 440 nm analogous with that of THPE (Figure 3b), except for electron-deficient imidazole (15) (Figure 3a). The inclusion of solvents rarely influenced on the photoluminescence as shown in THPE–13 and THPE–14 (Figure 3a). The absolute photoluminescence quantum yield (ΦF) of crystals were 0.49 (THPE), 0.24 (THPE–8), 0.39 (THPE–9), 0.71 (THPE–10), and 0.52 (THPE–11) as summarized in Table S2. This result clearly indicated that the photoluminescence property of the co-crystal strongly depends on the employed HBA.


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Figure 4. Molecular orbitals and corresponding orbital energy of molecules 1, THPE, and 8, and their crystals THPE–1 and THPE–8 calculated by density functional theory (DFT) and timedependent DFT (TDDFT) at the B3LYP/6-31+G(d) level using Gaussian 16.. To clarify the mechanism of photoluminescence, theoretical computations were conducted for 1, THPE, and 9, and their crystals THPE–1 and THPE–9, as shown in Figure 4 by density functional theory (DFT) and time-dependent DFT (TDDFT) at the B3LYP59,60/6-31+G(d) level using the Gaussian 16 program.61 For THPE–1 and THPE–9, the structures were extracted from their crystals. As a result of the calculations, the electron transitions from the highest occupied molecular orbital (HOMO) to the lowest unoccupied molecular orbital (LUMO) were predominantly anticipated in THPE–9 (3.38 eV, f = 0.3298) and HOMO → LUMO+2 in THPE–1 (3.49 eV, f = 0.3988). In the latter case, photo-induced electron transfer (PET) to the LUMO or LUMO+1, mainly located on the pyridine ring, would occur, which would lead to the observed photoluminescence quenching (Figure 3a) However, the HOMO and LUMO of THPE–9 totally located on the THPE moiety, thus the quenching pathway, including PET, could be suppressed. The LUMO energy in 1 (−1.06 eV) and 9 (−0.19 eV) were responsible for the difference of the electronic structure of the co-crystals, and their consequent photoluminescence


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properties, which is also true for co-crystals from HBAs 3–8 and 10–15, as revealed from the calculated HOMO and LUMO energy summarized in Table S3. For HBA 2, the generation of phenoxide anion and consequent reabsorption is presumably responsible for the quenching as evidenced from the coloration of the crystallization solution (Figure S2), while LUMO energy of 2 was as high as those of HBA 9–14.


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Conclusion In this study, we prepared hydrogen bonding-based co-crystals derived from THPE and various HBAs containing nitrogen atoms. By changing the HBA, the hydrogen bonding pattern or inclusion of crystallization solvents largely varied, depending on the size, position of nitrogen atoms, or basicity of the employed HBA, owing to the moderate hydrogen bonding ability of THPE. The photoluminescence properties derived from the AIE character of THPE were influenced by the adjacent HBA. Co-crystals derived from an imidazole derivative or DABCO exhibited intense photoluminescence, whereas those derived from pyridine derivatives and an electron-deficient imidazole derivative did not show any photoluminescence. Theoretical computations indicated that photo-induced electron transfer (PET) led to the quenching of the co-crystals derived from pyridine derivatives. These data convincingly suggested the possibility to control the photoluminescence property of co-crystals derived from AIEgen through other components in the co-crystal.

Supporting Information. The following files are available free of charge. Summary of crystallographic data (docx), CIF.

Corresponding Author *Kenta Kokado, *Kazuki Sada.


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Acknowledgments The authors acknowledge financial support from JSPS KAKENHI Grant Numbers JP15K17861, JP18H04495, Shorai Foundation for Science and Technology, Asahi Glass Foundation, and Ogasawara Foundation for the Promotion of Science & Engineering. The authors greatly appreciate Prof. T. Inabe and Prof. J. Harada for single crystal analysis, and Prof. M. Kato and Prof. A. Kobayashi for single crystal analysis and absolute photoluminescence quantum yield measurements.


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Emissive

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For Table of Contents Graphic Use Only

Control of Aggregation-Induced Emission from Tetraphenylethene Derivative through the Components in the Co-Crystal Takahiro Jimbo, Mikako Tsuji, Ryosuke Taniguchi, Kazuki Sada,* and Kenta Kokado* The photoluminescence property of a typical AIEgen, tetraphenylethene, in a co-crystal is controlled by another component of the co-crystal. The co-crystals derived from imidazole exhibit intense emission, while those from pyridine show no emission.


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Control of Aggregation-Induced Emission from a Tetraphenylethene

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