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Nghiên cứu cấu trúc và tính chất một số hệ vòng ngưng tụ chứa lưu huỳnh và silic ứng dụng trong chế tạo vật liệu quang điện.Nghiên cứu cấu trúc và tính chất một số hệ vòng ngưng tụ chứa lưu huỳnh và silic ứng dụng trong chế tạo vật liệu quang điện.Nghiên cứu cấu trúc và tính chất một số hệ vòng ngưng tụ chứa lưu huỳnh và silic ứng dụng trong chế tạo vật liệu quang điện.Nghiên cứu cấu trúc và tính chất một số hệ vòng ngưng tụ chứa lưu huỳnh và silic ứng dụng trong chế tạo vật liệu quang điện.Nghiên cứu cấu trúc và tính chất một số hệ vòng ngưng tụ chứa lưu huỳnh và silic ứng dụng trong chế tạo vật liệu quang điện.Nghiên cứu cấu trúc và tính chất một số hệ vòng ngưng tụ chứa lưu huỳnh và silic ứng dụng trong chế tạo vật liệu quang điện.Nghiên cứu cấu trúc và tính chất một số hệ vòng ngưng tụ chứa lưu huỳnh và silic ứng dụng trong chế tạo vật liệu quang điện.Nghiên cứu cấu trúc và tính chất một số hệ vòng ngưng tụ chứa lưu huỳnh và silic ứng dụng trong chế tạo vật liệu quang điện.Nghiên cứu cấu trúc và tính chất một số hệ vòng ngưng tụ chứa lưu huỳnh và silic ứng dụng trong chế tạo vật liệu quang điện.Nghiên cứu cấu trúc và tính chất một số hệ vòng ngưng tụ chứa lưu huỳnh và silic ứng dụng trong chế tạo vật liệu quang điện.Nghiên cứu cấu trúc và tính chất một số hệ vòng ngưng tụ chứa lưu huỳnh và silic ứng dụng trong chế tạo vật liệu quang điện.
BỘ GIÁO DỤC VÀ ĐÀO TẠO TRƯỜNG ĐẠI HỌC SƯ PHẠM HÀ NỘI - TRẦN NGỌC DŨNG Nghiên cứu cấu trúc tính chất số hệ vòng ngưng tụ chứa lưu huỳnh silic ứng dụng chế tạo vật liệu quang điện LUẬN ÁN TIẾN SĨ Hà Nội - 2022 BỘ GIÁO DỤC VÀ ĐÀO TẠO TRƯỜNG ĐẠI HỌC SƯ PHẠM HÀ NỘI - TRẦN NGỌC DŨNG Nghiên cứu cấu trúc tính chất số hệ vòng ngưng tụ chứa lưu huỳnh silic ứng dụng chế tạo vật liệu quang điện Chuyên ngành: Hóa lý thuyết Hóa lý Mã số: 9440119 Người hướng dẫn khoa học : PGS.TS Nguyễn Thị Minh Huệ PGS.TS Nguyễn Hiển Hà Nội - 2022 LỜI CAM ĐOAN Tôi xin cam đoan luận án kết nghiên cứu cá nhân Các số liệu tài liệu trích dẫn luận án thực cách trung thực Kết nghiên cứu không trùng với công trình cơng bố trước Tơi xin chịu trách nhiệm với lời cam đoan Hà Nội, tháng năm 2022 Nghiên cứu sinh Trần Ngọc Dũng LỜI CẢM ƠN ===**=== Trước tiên, em xin bày tỏ lòng biết ơn sâu sắc trân trọng tới cô PGS.TS Nguyễn Thị Minh Huệ thầy PGS.TS Nguyễn Hiển bảo, hướng dẫn, động viên giúp đỡ em tận tình suốt thời gian thực hoàn thành luận án Em xin chân thành cảm ơn hỗ trợ nhiệt tình NCS Nguyễn Văn Tráng, Viện Kỹ thuật nhiệt đới, Viện Hàn lâm Khoa học Công nghệ Việt Nam suốt thời gian em hồn thành luận án Em xin tỏ lịng biết ơn sâu sắc chân thành đến toàn thể Thầy, Cơ Bộ mơn Hóa lý thuyết Hóa lý Bộ Mơn Hố học Hữu Thầy, Cô, anh chị làm việc Trung tâm Khoa học tính tốn, Trường Đại học Sư phạm Hà Nội tạo điều kiện cho em trình thực đề tài Cuối cùng, em xin gửi lời biết ơn sâu sắc tới người thân gia đình ln động viên hỗ trợ em để em tập trung trí lực hồn thành luận án Xin trân trọng cảm ơn! Hà Nội, tháng năm 2022 Nghiên cứu sinh Trần Ngọc Dũng MỤC LỤC MỤC LỤC .iii DANH MỤC CÁC KÍ HIỆU VIẾT TẮT v MỤC LỤC HÌNH ẢNH vii MỤC LỤC BẢNG x MỞ ĐẦU 1 Lý chọn đề tài .1 Mục đích, nhiệm vụ nghiên cứu 3 Đối tượng phạm vi nghiên cứu Ý nghĩa khoa học thực tiễn luận án Những điểm luận án CHƯƠNG 1: TỔNG QUAN 1.1 Cơ sở lý thuyết vật liệu quang điện hữu 1.1.1 Cấu tạo chế hoạt động đi-ốt phát quang hữu .5 1.1.2 Cấu tạo chế hoạt động pin mặt trời chất màu nhạy quang 11 1.2 Cơ sở lý thuyết hoá học lượng tử 16 1.3 Cơ sở lý thuyết phản ứng Heck 19 1.4 Hệ chất nghiên cứu .22 1.4.1 Hệ chất ngưng tụ chứa lưu huỳnh 22 1.4.2 Hệ chất ngưng tụ chứa silic 28 1.4.3 Tình hình nghiên cứu hợp chất ngưng tụ chứa lưu huỳnh .33 1.4.4 Tình hình nghiên cứu hợp chất ngưng tụ chứa silic .36 CHƯƠNG 2: PHƯƠNG PHÁP NGHIÊN CỨU 39 2.1 Phương pháp nghiên cứu lý thuyết .39 2.1.1 Phương pháp phiếm hàm mật độ 39 2.1.2 Phương pháp phiếm hàm mật độ phụ thuộc thời gian 43 2.1.3 Bộ hàm sở .45 2.1.4 Khả truyền dẫn điện tích .45 2.1.5 Phương pháp tính tốn hóa học lượng tử .46 2.2 Phương pháp nghiên cứu thực nghiệm .47 2.2.1 Hóa chất 48 2.2.2 Dụng cụ thiết bị 48 2.2.3 Quy trình phản ứng alkenyl hóa BDT 48 2.2.4 Phân tích cấu trúc sản phẩm 49 CHƯƠNG 3: KẾT QUẢ NGHIÊN CỨU VÀ THẢO LUẬN .50 3.1 Hệ chất ngưng tụ chứa lưu huỳnh .50 3.1.1 Nghiên cứu cấu trúc tính chất hợp chất lưỡng cực dựa dibenzothiophene ứng dụng làm vật liệu chất mang OLED hệ thứ hai 50 3.1.2 Tổng hợp 2-Alkenylbenzo[1,2-b:4,5-b’]dithiophene hệ xúc tác Pd/Cu/Ag nghiên cứu cấu trúc phương pháp phổ thực nghiệm tính tốn lý thuyết 61 3.1.3 Thiết kế hệ chất bithiophene liên hợp chứa silole số dị vòng năm cạnh cho vật liệu quang điện 69 3.2 Hệ ngưng tụ chứa silic 94 3.2.1 Nghiên cứu cấu trúc tính chất quang điện số dẫn suất dithienosilole 94 3.2.2 Nghiên cứu lý thuyết ảnh hưởng cầu nối π hệ chất hữu dạng D-π-A ứng dụng cho pin mặt trời polymer 111 KẾT LUẬN CHUNG 120 ĐỊNH HƯỚNG NGHIÊN CỨU TIẾP THEO .121 DANH MỤC CƠNG TRÌNH ĐÃ CƠNG BỐ .122 TÀI LIỆU THAM KHẢO 123 DANH MỤC CÁC KÍ HIỆU VIẾT TẮT Viết tắt HOMO Nguyên tiếng Anh Highest occupied Tạm dịch Orbital phân tử bị chiếm cao LUMO molecular orbital Lowest unoccupied Orbital phân tử không bị OLED molecular orbital Organic light emitting chiếm thấp Đi-ốt phát quang hữu DSSC diode Dye sensitized solar cell Pin mặt trời chất màu nhạy OPV OFET Organic photovoltaics Organic field effect quang Quang điện hữu Transistor hiệu ứng trường OTFT transistor Organic thin-film hữu Transistor màng mỏng hữu OSC AIE transistor Organic semiconductors Aggregation induced Chất bán dẫn hữu Phát xạ tập hợp ACQ emission Aggregation caused Dập tắt tập hợp HBMC quench Heteronuclear Multiple Phổ tương quan liên kết HSQC Bond Correlation Heteronuclear Single Phổ tương quan lượng tử đơn DFT Quantum Coherence Density functional nhân Thuyết phiếm hàm mật độ TD-DFT theory Time-dependent Thuyết phiếm hàm mật độ density functional phụ thuộc thời gian TTA theory Triplet-triplet Triệt tiêu triplet-triplet HLCT annihilation Hybridized local and Lai hoá cục chuyển TADF charge transfer Thermally activated điện tích Huỳnh quang trễ hoạt hóa IQE delayed fluorescence Internal quantum nhiệt Hiệu suất lượng tử nội EQE efficiency External quantum Hiệu suất lượng tử ngoại PLQE efficiency Photoluminescence Hiệu suất phát quang lượng SOMO quantum efficiency Singly occupied tử Orbital phân tử singlet bị SUMO molecular orbital Singly unoccupied chiếm Orbital phân tử singlet không LDA molecular orbital Local density bị chiếm Xấp xỉ mật độ địa phương GGA approximation Generalized gradient Gradient tổng quát EA IP EHOMO ELUMO Egap S0 S1 approximation Electron affinity Ionization potential HOMO energy LUMO energy Band-gap energy Singlet ground state First singlet excited Ái lực electron Thế oxi hoá Năng lượng HOMO Năng lượng LUMO Năng lượng HOMO-LUMO Trạng thái singlet Trạng thái kích thích singlet T1 state thứ First triplet excited state Trạng thái kích thích triplet ES0 Singlet ground state thứ Năng lượng trạng thái singlet ES1 energy First singlet excited Năng lượng trạng thái kích ET1 state energy thích singlet thứ First triplet excited state Năng lượng trạng thái kích λh energy Hole reorganization thích triplet thứ Năng lượng tái tổ hợp cho λe energy Electron reorganization electron Năng lượng tái tổ hợp cho lỗ energy trống 147 DANH MỤC CƠNG TRÌNH ĐÃ CƠNG BỐ 1) Nguyen Van Trang, Tran Ngoc Dung, Tran Thi Thoa, Dinh Thi Mai Thanh, and Nguyen Thi Minh Hue "Stability and Semi‐ Conductive Property of Some Derivatives of Mono‐and Di‐Silole: A Theoretical Study." Vietnam Journal of Chemistry 57, no (2019): 507-13 2) Tran Ngoc Dung, Nguyen Van Trang, Dinh Thi Mai Thanh, Nguyen Thi Van Khanh, Hien Nguyen, and Hue Minh Thi Nguyen "A Facile Regioselectively Synthesis of 2-Alkenylbenzo [1, 2-B: 4, 5B’] Dithiophene by Pd/Cu/Ag-Catalyzed Ch Functionalization." ChemistrySelect 5, no 19 (2020): 5581-86 3) Tran Ngoc Dung, Nguyen Van Trang, Tran Thi Thoa, Phan Thi Thuy, Dinh Thi Mai Thanh, and Nguyen Thi Minh Hue "Theoretical Study of Structures and Properties of Some Silole Compounds." Vietnam Journal of Chemistry 58, no (2020): 21220 4) Nguyen Van Trang, Tran Ngoc Dung, Ngo Tuan Cuong, Le Thi Hong Hai, Daniel Escudero, Minh Tho Nguyen, and Hue Minh Thi Nguyen "Theoretical Study of a Class of Organic D-Π-a Dyes for Polymer Solar Cells: Influence of Various Π-Spacers." Crystals 10, no (2020): 163 5) Nguyen Van Trang, Tran Ngoc Dung, Long Van Duong, My Phuong Pham-Ho, Hue Minh Thi Nguyen, and Minh Tho Nguyen "Structural, Electronic, and Optical Properties of Some New Dithienosilole Derivatives." Structural Chemistry 31, no (2020): 2215-25 6) Nguyen Van Trang, Nguyen Minh Tam, Tran Ngoc Dung, and Minh Tho Nguyen "A Theoretical Design of Bipolar Host Materials 148 for Blue Phosphorescent Oled." Journal of Molecular Graphics and Modelling 105 (2021): 107845 7) Hue Minh Thi Nguyen, Tran Ngoc Dung, Nguyen Van Trang, Ngo Tuan Cuong, Nguyen Van Minh, Hien Nguyen, and Minh Tho Nguyen "Design of Fused Bithiophene Systems Containing Silole and Five-Membered Heterocycles for Optoelectronic Materials." 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