Design and Synthesis of Boron Containing Small Molecules for Organic Photovoltaics

Natural resources have been attracted as alternative energy which is cost effective, eco-friendly and infinite supply. Organic solar cell is one of them using solar energy. Organic materials for organic photovoltaics (OPV) have been developed for increasing their power conversion efficiency (PCE). Nowadays, small molecules for OPV have many strengths which are more reproductive, high carrier mobility and easy to control the bandgap energy than polymer based organic materials. Boron containing materials are well known for good stability, having narrow absorption such as 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) derivatives and boron subphthalocyanine (SubPc). In this study, a new A-π-A type small molecules based on thienyl complex (π-spacer) and DPP or rhodanine derivatives as acceptor (A) were designed and synthesized employing Pd-catalyzed Stille cross-coupling reaction as a key step. The synthesized boron containing small molecules exhibited high electron affinity, which indicates reducing band gap energy, and broad band absorption. Herein, we report the synthetic methods for the preparation of a new type of thiazole-borane complex and their application for solar cell.;천연 자원은 경제적, 친환경적이고 무한하다는 점에서 대체에너지로써 각광을 받고있다. 유기태양전지는 태양에너지를 이용한 것 중 하나이며, 태양전지의 효율을 높이기 위해 유기태양전지용 물질 연구들이 진행되고 있다. 현재, 유기태양전지용 단분자 물질이 고분자 물질보다 재현성과 높은 전자 이동 및 밴드갭 에너지를 쉽게 조절할 수 있다는 장점이 있다. BODIPY, SubPc와 같이, 보론이 포함된 물질은 안정성이 좋고 높은 흡수파장대를 가지고 있는 것으로 알려져있다. 본 연구에서는 팔라듐 촉매를 이용한 스틸리-커플링 반응을 통해 thiazole-borane complex를 π-spacer로 사용하고 Acceptor인 DPP와 Rhodanine 물질을 A-π-A, D-A-π-A-D, A-D-π-D-A 타입의 형태로 물질 디자인 및 합성을 진행하였다. 보론이 포함된 합성 단분자 물질들은 높은 전자 친화도를 보이며, 이것은 밴드갭 에너지를 줄이고 넓은 흡수파장대를 가지는 것을 의미한다. thiazole-borane complex를 이용해 만든 새로운 단분자 물질 합성 방법과 태양전지에 응용한 결과에 대해 소개한다.1 Introduction 2 1.1 General Information of Organic Photovoltaics 1.2 Working Principles of Organic Photovoltaics 1.3 The Purpose of Boron containing Materials Study 2 Results and Discussion 8 2.1 DPP Based Boron-containing Small Molecules 2.2 Synthetic Routes for DPP based Boron-containing Small Molecules 2.3 Rhodanine Based Boron-containing Small Molecules 2.4 Synthetic Routes for Rhodanine Based Boron-containing Small Molecules 2.5 Optical and Electronical Properties of Synthesized Small Molecules 2.5.1 UV-Vis Spectroscopy Data 2.5.2 Cylic Voltammetry Data 2.5.3 Energy Band Gap 2.5.4 Photovoltaic Performances 3 Conclusion 24 Experimental Section-Supporting Information 25 A. Materials & Instruments B. Synthesis and Characterization of Small Molecules B.1 Synthesis of SDB- 1 B.2 Synthesis of SDB- 2 B.3 Synthesis of SDB- 4 B.4 Synthesis of 1b B.5 Synthesis of 2b B.6 Synthesis of 3b B.7 Synthesis of SDB-Rh 1 B.8 Synthesis of SDB-Rh 2 B.9 Synthesis of SDB-Rh 3 Appendix NMR Spectra- 43 Figure.1 1H and 13C NMR Spectrum of Compound SDB- 1 Figure.2 1H and 13C NMR Spectrum of Compound SDB- 2 Figure.3 1H and 13C NMR Spectrum of Compound SDB- 4 Figure.4 1H and 13C NMR Spectrum of Compound SDB-Rh1CHO (1b) Figure.5 1H and 13C NMR Spectrum of Compound SDB-Rh2CHO (2b) Figure.6 1H and 13C NMR Spectrum of Compound SDB-Rh3CHO (3b) Figure.7 1H and 13C NMR Spectrum of Compound SDB-Rh 1 Figure.8 1H and 13C NMR Spectrum of Compound SDB-Rh 2 Figure.9 1H and 13C NMR Spectrum of Compound SDB-Rh 3 Abstract (in Korean) 53 Reference 5

Gold(I)-catalyzed synthesis of 2-arylthieno[3,2-b]pyridine-5(4H)-ones and studies toward a small-molecule fluorescent probe for vimentin

Molecular fluorescence is a rapidly growing research field that provides an outstanding tool for nondestructive investigations in biology, biomedical science, environment and drug discovery. Moreover, there is high demand of fluorescent materials in electronic and energy industry for applications in OLED (organic light-emitting diode) and organic solar cell. Accordingly, we have witnessed remarkable advances in these fields over the last several decades and we have now an access to a variety of fluorescent scaffolds, which are commonly outsourced as the prototypes to design new fluorophores. In this poster, we describe a synthetic method for the access to a series of fluorescent thieno[3,2-b]pyridine-5(4H)-one derivatives via a gold(I)-catalyzed 6-endo-dig cycloisomerization of Nthiophen-3-yl alkynylamides. Investigation on the photophysical properties of the newly synthesized fluorophores revealed that the photophysical properties are chemically tunable by an appropriate choice of functional group on the thieno[3,2-b]pyridine-5(4H)-one scaffold (emission maxima up to 559 nm, Stokes shifts up to 197 nm, and quantum yields up to 98%). Next, our endeavor aimed at establishing a small-molecule fluorescent probe for vimentin is described which is based on the conjugate of withaferin A (a natural product originally derived from Withania somnifera) and a fluorescent thieno[3,2-b]pyridine-5(4H)-one derivative. Vimentin is aerials in electronic and energy industry for applications in OLED (organic light-emitting diode) and organic solar cell. Accordingly, we have witnessed remarkable advances in these fields over the last several decades and we have now an access to a variety of fluorescent scaffolds, which are commonly outsourced as the prototypes to design new fluorophores. In this poster, we describe a synthetic method for the access to a series of fluorescent thieno[3,2-b]pyridine-5(4H)-one derivatives via a gold(I)-catalyzed 6-endo-dig cycloisomerization of Nthiophen-3-yl alkynylamides. Investigation on the photophysical properties of the newly synthesized fluorophores revealed that the photophysical properties are chemically tunable by an appropriate choice of functional group on the thieno[3,2-b]pyridine-5(4H)-one scaffold (emission maxima up to 559 nm, Stokes shifts up to 197 nm, and quantum yields up to 98%). Next, our endeavor aimed at establishing a small-molecule fluorescent probe for vimentin is described which is based on the conjugate of withaferin A (a natural product originally derived from Withania somnifera) and a fluorescent thieno[3,2-b]pyridine-5(4H)-one derivative. Vimentin is a1

Fluorescent probe for F-actin detection and use thereof

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