Theoretical Investigation of Hole and Electron Transport Properties for Hydroxy-Tetraphenylimidazole Derivatives

Fan Liao; Xiaoying Cui; Chungang Min; Aimin Ren

doi:10.3788/AOS221676

Journals >Acta Optica Sinica >Volume 43 >Issue 5 >Page 0530001 > Article

Acta Optica Sinica
Vol. 43, Issue 5, 0530001 (2023)

Theoretical Investigation of Hole and Electron Transport Properties for Hydroxy-Tetraphenylimidazole Derivatives

Fan Liao¹, Xiaoying Cui², Chungang Min^2、*, and Aimin Ren^3、**

Author Affiliations

¹Faculty of Materials Science and Engineering, Kunming University of Science and Technology, Kunming 650093, Yunnan, China

²Research Center for Analysis and Measurement, Kunming University of Science and Technology, Kunming 650093, Yunnan, China

³Institute of Theoretical Chemistry, College of Chemistry, Jilin University, Changchun 130021, Jilin, China

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DOI: 10.3788/AOS221676 Cite this Article Set citation alerts

Fan Liao, Xiaoying Cui, Chungang Min, Aimin Ren. Theoretical Investigation of Hole and Electron Transport Properties for Hydroxy-Tetraphenylimidazole Derivatives[J]. Acta Optica Sinica, 2023, 43(5): 0530001 Copy Citation Text

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Fig. 1. Schematic diagram of designed molecular structures

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Fig. 2. Kohn-Sham frontier orbitals for HPI-TPA, HPI-PCz, HPI-DMAC, HPI-PTZ, HPI-PXZ and HPI-InPz predicted by PBE0/6-31G(d, p) method

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Fig. 3. Absorption spectra simulated by Gaussian function

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Derivative	Absorption spectrum				Emission spectrum
Derivative	Experiment^［16］	B3LYP	PBE0	CAM-B3LYP	Experiment^［16］	B3LYP	PBE0	CAM-B3LYP
HPI-TPA	338	364	350	302	402	478	448	351
HPI-PCz	339	381	358	285	490	540	498	358

Table 1. Absorption and emission spectra of HPI-TPA and HPI-PCz in experimental and theoretical calculation obtained by combining B3LYP, PBE0 and CAM-B3LYP with 6-31G(d, p) basis set

Segment	Orbital	HPI-TPA	HPI-PCz	HPI-DMAC	HPI-PTZ	HPI-PXZ	HPI-InPz
HPI	HOMO-2	97.0	2.5	99.8	99.9	99.8	99.9
	HOMO-1	7.0	3.6	0	0	0	0
	HOMO	1.0	99.3	0	0	0.1	0
	LUMO	49.4	53.4	54.3	53.0	53.2	53.1
	LUMO+1	56.2	58.0	59.7	56.4	57.6	56.7
	LUMO+2	92.5	86.7	86.5	86.5	86.3	87.3
	LUMO+3	18.4	0.1	67.4	23.1	18.2	12.0
	LUMO+6	0.4	20.4	91.4	79.6	89.0	4.0
R-up	HOMO-2	3.0	85.3	0.2	0.1	0.2	0
	HOMO-1	92.8	11.5	0	100.0	100.0	100.0
	HOMO	0.2	0.5	100.0	0	0	0
	LUMO	7.9	23.0	24.5	24.9	23.8	23.5
	LUMO+1	33.3	18.6	16.7	18.7	18.6	19.2
	LUMO+2	6.7	10.6	10.4	11.2	10.6	10.1
	LUMO+3	75.5	99.9	19.6	11.7	78.6	86.1
	LUMO+6	99.6	47.5	6.0	15.1	7.5	95.6
R-down	HOMO-2	0	12.2	0	0	0	0
	HOMO-1	0.2	84.9	100.0	0	0	0
	HOMO	98.8	0.2	0	100.0	99.9	100.0
	LUMO	42.7	23.6	21.2	22.1	23.0	23.4
	LUMO+1	10.5	23.4	23.5	24.8	23.8	24.1
	LUMO+2	0.8	2.7	3.1	2.3	3.1	2.6
	LUMO+3	6.1	0	13.0	65.2	3.2	1.9
	LUMO+6	0	32.1	2.6	5.3	3.5	0.3

Table 2. Contribution of electron densities of different segments to orbitals in HPI-TPA, HPI-PCz, HPI-DMAC, HPI-PTZ, HPI-PXZ and HPI-InPz

Compound	HPI-TPA	HPI-PCz	HPI-DMAC	HPI-PTZ	HPI-PXZ	HPI-InPz
E_HOMO	-5.27	-5.56	-5.24	-5.29	-4.98	-4.81
E_LUMO	-1.12	-1.46	-1.46	-1.56	-1.56	-1.57
ΔE_H‑L	4.15	4.10	3.78	3.73	3.42	3.24

Table 3. HOMO energy, LUMO energy and HOMO-LUMO energy gap of studied compounds

Compound	I_P，v	I_P，a	P_HE	E_A，v	E_A，a	P_EE	λ_hole	λ_electron
HPI-TPA	6.51	6.01	5.98	0.34	0.50	0.77	0.53	0.43
HPI-PCz	6.40	6.35	6.29	0.50	0.76	0.99	0.11	0.49
HPI-DMAC	6.09	6.01	5.98	0.49	0.76	0.99	0.11	0.50
HPI-PTZ	6.14	5.95	5.75	0.58	0.85	1.09	0.39	0.51
HPI-PXZ	5.87	5.81	5.76	0.58	0.85	1.09	0.11	0.51
HPI-InPz	5.60	5.55	5.49	0.61	0.87	1.11	0.11	0.50

Table 4. Ionization potentials, electron affinities, extraction potentials and reorganization energies for studied compounds

Compound	Electronic transition	Wavelength /nm	f	Main configuration
HPI-TPA	S₀→S₁	350（338）^［16］	0.9385	HOMO-1→LUMO（75.8%）
	S₀→S₁	350（338）^［16］	0.9385	HOMO→LUMO+1（15.3%）
	S₀→S₂	342	0.2341	HOMO-2→LUMO（11.8%）
	S₀→S₂	342	0.2341	HOMO→LUMO（77.5%）
	S₀→S₃	340	0.1554	HOMO-2→LUMO（83.4%）
	S₀→S₃	340	0.1554	HOMO→LUMO（10.0%）
HPI-PCz	S₀→S₁	358	0.0043	HOMO→LUMO（98.7%）
	S₀→S₂	340（339）^［12］	0.1363	HOMO-2→LUMO（5.3%）
				HOMO-1→LUMO（13.5%）
				HOMO→LUMO+1（73.5%）
	S₀→S₃	338	0.4745	HOMO-2→LUMO（47.6%）
				HOMO-1→LUMO（16.0%）
				HOMO-1→LUMO+1（12.2%）
				HOMO→LUMO+1（18.9%）
HPI-DMAC	S₀→S₁	398	0.0007	HOMO→LUMO（81.3%）
	S₀→S₁	398	0.0007	HOMO→LUMO+1（11.5%）
	S₀→S₂	381	0.0007	HOMO-1→LUMO（71.3%）
	S₀→S₂	381	0.0007	HOMO-1→LUMO+1（23.4%）
	S₀→S₃	358	0.0046	HOMO-2→LUMO（98.8%）
	S₀→S₁₀	309	0.2398	HOMO-2→LUMO+2（93.7%）
HPI-PTZ	S₀→S₁	397	0.0002	HOMO→LUMO（72.9%）
	S₀→S₁	397	0.0002	HOMO→LUMO+1（21.7%）
	S₀→S₂	393	0.0001	HOMO-1→LUMO（80.3%）
	S₀→S₂	393	0.0001	HOMO-1→LUMO+1（12.7%）
	S₀→S₃	363	0.0038	HOMO-2→LUMO（98.9%）
	S₀→S₁₀	310	0.1613	HOMO-2→LUMO+2（61.1%）
	S₀→S₁₀	310	0.1613	HOMO-1→LUMO+2（28.6%）
HPI-PXZ	S₀→S₁	444	0.0186	HOMO→LUMO（74.1%）
	S₀→S₂	442	0.0012	HOMO-1→LUMO（79.4%）
	S₀→S₂	442	0.0012	HOMO-1→LUMO+1（13.8%）
	S₀→S₃	391	0.0014	HOMO→LUMO（16.5%）
	S₀→S₃	391	0.0014	HOMO→LUMO+1（81.7%）
	S₀→S₁₄	310	0.2415	HOMO-2→LUMO+2（92.7%）
HPI-InPz	S₀→S₁	466	0.0043	HOMO→LUMO（77.5%）
	S₀→S₁	466	0.0043	HOMO→LUMO+1（18.5%）
	S₀→S₂	462	0.0049	HOMO-1→LUMO（81.9%）
	S₀→S₂	462	0.0049	HOMO-1→LUMO+1（12.6%）
	S₀→S₃	411	0.0006	HOMO→LUMO（20.2%）
	S₀→S₃	411	0.0006	HOMO→LUMO+1（78.2%）
	S₀→S₉	357	0.1086	HOMO-1→LUMO+3（11.9%）
	S₀→S₉	357	0.1086	HOMO-1→LUMO+6（66.7%）

Table 5. Absorption spectra, oscillator strengths and main transition configurations obtained by TD PBE0/6-31G(d, p) method

Compound	Wavelength /nm	f	Main configuration
HPI-TPA	448（402）^［16］	0.1348	HOMO→LUMO（96.8%）
HPI-PCz	498（490）^［16］	0.0022	HOMO→LUMO（99.5%）
HPI-DMAC	502	0	HOMO→LUMO（96.9%）
HPI-PTZ	605	0	HOMO→LUMO（97.3%）
HPI-PXZ	600	0	HOMO→LUMO（97.0%）
HPI-InPz	643	0	HOMO→LUMO（97.3%）

Table 6. Emission wavelengths, oscillator strengths, main transition orbitals and transition coefficients of studied compounds

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