Novel naphthalene-diimide-based small molecule with a bithiophene linker for use in organic field-effect transistors

Ha, Yeon Hee,Oh, Jong Gyu,Park, Sejin,Kwon, Soon-Ki,An, Tae Kyu,Jang, Jaeyoung,Kim, Yun-Hi Elsevier 2018 ORGANIC ELECTRONICS Vol.63 No.-

<P><B>Abstract</B></P> <P>We report on the synthesis and characterization of a novel naphthalene diimide (NDI)-based small molecule with a bithiophene linker unit, NDI-BT-NDI-EH, for application as a solution-processable <I>n</I>-channel active material in organic field-effect transistors (OFETs). NDI-BT-NDI-EH was synthesized <I>via</I> the Stille coupling reaction and the bithiophene linker unit was introduced as a rotatable linker between two NDI cores to improve the solubility of NDI-BT-NDI-EH while maintaining its high field-effect mobility. We found that the crystallinity and molecular ordering of NDI-BT-NDI-EH thin films could be improved by thermal annealing; a moderate annealing temperature of 120 °C appeared to be optimal for promoting self-organization among the NDI-BT-NDI-EH molecules. The NDI-BT-NDI-EH molecules in thermally annealed thin films mainly adopted an edge-on orientation with improved <I>π</I>-<I>π</I> stacking on the surface of octyltrichlorosilane-treated SiO<SUB>2</SUB> substrates, which is favorable for lateral charge transport. As a result, the optimally annealed NDI-BT-NDI-EH OFET exhibited evident <I>n</I>-type OFET characteristics with high field-effect mobilities of up to 0.016 cm<SUP>2</SUP> V<SUP>−1</SUP> s<SUP>−1</SUP> and an on/off ratio of 1.4 × 10<SUP>5</SUP>.</P> <P><B>Highlights</B></P> <P> <UL> <LI> A novel NDI-based organic small molecular semiconductor is synthesized <I>via</I> the Stille coupling reaction. </LI> <LI> A rotatable bithiophene linker unit in NDI-BT-NDI-EH improves solubility while maintaining high carrier mobility. </LI> <LI> Thermally annealed NDI-BT-NDI-EH molecules show an edge-on orientation with increased crystallinity. </LI> <LI> NDI-BT-NDI-EH-based <I>n</I>-type OFETs exhibit high performance with <I>μ</I> <SUB> <I>e</I> </SUB> of up to 0.016 cm<SUP>2</SUP> V<SUP>−1</SUP> s<SUP>−1</SUP>. </LI> </UL> </P> <P><B>Graphical abstract</B></P> <P>[DISPLAY OMISSION]</P>

Functional Expression of the Internal Rotenone-Insensitive NADH-Quinone Oxidoreductase (NDI1) Gene of Saccharomyces cerevisiae in Human HeLa Cells

Byoung Boo Seo 사단법인 한국동물생명공학회 2010 한국동물생명공학회지 Vol.25 No.1

Many studies propose that dysfunction of mitochondrial proton-translocating NADH-ubiquinone oxidoreductase (complex I) is associated with neurodegenerative disorders, such as Parkinson's disease and Huntington's disease. Mammalian mitochondrial proton-translocating NADH-quinone oxidoreductase (complex I) consists of at least 46 different subunits. In contrast, the NDI1 gene of Saccharomyces cerevisiae is a single subunit rotenone-insensitive NADH-quinone oxidoreductase that is located on the matrix side of the inner mitochondrial membrane. With a recombinant adeno-associated virus vector carrying the NDI1 gene (rAAV-NDI1) as the gene delivery method, we were able to attain high transduction efficiencies even in the human epithelial cervical cancer cells that are difficult to transfect by lipofection or calcium phosphate precipitation methods. Using a rAAV-NDI1, we demonstrated that the Ndi1 enzyme is successfully expressed in HeLa cells. The expressed Ndi1 enzyme was recognized to be localized in mitochondria by confocal immunofluorescence microscopic analyses and immunoblotting. Using digitonin-permeabilized cells, it was shown that the NADH oxidase activity of the NDI1-transduced HeLa cells were not affected by rotenone which is inhibitor of complex I, but was inhibited by flavone and antimycin A. The NDI1-transduced cells were able to grow in media containing rotenone. In contrast, control cells that did not receive the NDI1 gene failed to survive. In particular, in the NDI1-transduced cells, the yeast enzyme becomes integrated into the human respiratory chain. It is concluded that the NDI1 gene provides a potentially useful tool for gene therapy of mitochondrial diseases caused by complex I deficiency.

Functional Expression of Saccharomyces cerevisiae NADH-quinone Oxidoreductase (NDI1) Gene in the AML12 Mouse Liver Hepatocytes for the Applying Embryonic Stem Cell

Seo, Byoung-Boo,Park, Hum-Dai The Korean Society of Animal Reproduction 2011 Reproductive & developmental biology Vol.35 No.4

Mitochondria diseases have been reported to involve structural and functional defects of complex I-V. Especially, many of these diseases are known to be related to dysfunction of mitochondrial proton-translocating NADH-ubiquinone oxidoreductase (complex I). The dysfunction of mitochondria complex I is associated with neurodegenerative disorders, such as Parkinson's disease, Huntington's disease, and Leber's hereditary optic neuropathy (LHON). Mammalian mitochondrial proton-translocating NADH-quinone oxidoreductase (complex I) is largest and consists of at least 46 different subunits. In contrast, the NDI1 gene of Saccharomyces cerevisiae is a single subunit rotenone-insensitive NADH-quinone oxidoreductase that is located on the matrix side of the inner mitochondrial membrane. The Saccharomyces cerevisiae NDI1 gene using a recombinant adeno-associated virus vector (rAAV-NDI1) was successfully expressed in AML12 mouse liver hepatocytes and the NDI1-transduced cells were able to grow in media containing rotenone. In contrast, control cells that did not receive the NDI1 gene failed to survive. The expressed Ndi1 enzyme was recognized to be localized in mitochondria by confocal immunofluorescence microscopic analyses and immunoblotting. Using digitonin-permeabilized cells, it was shown that the NADH oxidase activity of the NDI1-transduced cells was not affected by rotenone which is inhibitor of complex I, but was inhibited by antimycin A. Furthermore, these results indicate that Ndi1 can be functionally expressed in the AML12 mouse liver hepatocytes. It is conceivable that the NDI1 gene is powerful tool for gene therapy of mitochondrial diseases caused by complex I deficiency. In the future, we will attempt to functionally express the NDI1 gene in mouse embryonic stem (mES) cell.

Impact of Incorporating Nitrogen Atoms in Naphthalenediimide-Based Polymer Acceptors on the Charge Generation, Device Performance, and Stability of All-Polymer Solar Cells

Kim, Sang Woo,Wang, Yang,You, Hoseon,Lee, Wonho,Michinobu, Tsuyoshi,Kim, Bumjoon J. American Chemical Society 2019 ACS APPLIED MATERIALS & INTERFACES Vol.11 No.39

<P>Substitution of C atoms in a polymer backbone by N atoms allows for the facile tuning of the energy levels as well as the backbone conformation and packing structures of conjugated polymers. Herein, we report a series of three polymer acceptors (<I>P</I><SUB>A</SUB>s) with N atoms introduced at different positions of the backbone and investigate how these N atoms affect the device performances of all-polymer solar cells (all-PSCs). The three <I>P</I><SUB>A</SUB>s, namely, P(NDI2DT-BTT), P(NDI2DT-PTT), and P(NDI2DT-BTTz), are composed of naphthalenediimide (NDI)-based and benzothiadiazole (BT)-based derivatives (dithiophene-BT (BTT), dithiophene-thiadiazolepyridine (PTT), and dithiazole-BT (BTTz)). The PTT and BTTz units are synthesized by replacing the C atoms in BT and thiophene, respectively, with N atoms, which effectively tune the optical, electrochemical, and charge-transporting properties of the corresponding <I>P</I><SUB>A</SUB>s. The all-PSCs using poly[(2,6-(4,8-bis(5-(2-ethylhexyl)thiophen-2-yl))benzo[1,2-<I>b</I>:4,5-<I>b</I>′]dithiophene)-<I>co</I>-(1,3-di(5-thiophene-2-yl)-5,7-bis(2-ethylhexyl)benzo[1,2-<I>c</I>:4,5-<I>c</I>′]dithiophene-4,8-dione)] (PBDB-T) as a polymer donor and P(NDI2DT-PTT) as <I>P</I><SUB>A</SUB> exhibit a significantly enhanced power conversion efficiency (PCE) of 6.95%, whereas the all-PSCs based on the other <I>P</I><SUB>A</SUB>s show relatively lower PCEs (6.02% for PBDB-T:P(NDI2DT-BTT) and 1.43% for PBDB-T:P(NDI2DT-BTTz)). The high PCE of the PBDB-T:P(NDI2DT-PTT) device is due to the superior charge transfer and charge dissociation, resulting from the closely matched energy levels between PBDB-T and P(NDI2DT-PTT), as well as a more favorable bulk heterojunction morphology with improved miscibility. Importantly, the P(NDI2DT-PTT)-based all-PSC device shows improved air stability compared to the P(NDI2DT-BTT)-based device, which is most likely due to a decreased lowest unoccupied molecular orbital level of the <I>P</I><SUB>A</SUB>. Our findings suggest that the incorporation of N atoms into the <I>P</I><SUB>A</SUB>s is an effective strategy for improving the efficiency and stability of all-PSCs.</P> [FIG OMISSION]</BR>

퇴행성 경추 디스크 질환에 대한 한국판 목 장애 설문지의 비교

조윤재,최민준,김한솔,고태식,이정섭 대한척추외과학회 2024 대한척추외과학회지 Vol.31 No.2

연구 계획: 전향적 연구목적: 두 가지 한국판 목 장애 설문지 결과의 타당성을 영상학적 소견과 삶의 질 점수를 비교 분석하여 입증하고자 함. 선행 연구문헌의 요약: 두 가지 목 장애 설문지에 대한 많은 연구가 있으나 두 설문지를 비교하는 연구는 드물다. 대상 및 방법: 단일 레벨 퇴행성 경추 디스크 질환(DCDD) 환자들에게 한국판 Neck Disability Index (NDI), Neck Pain and Disability Scale (NPDS) 그리고Short Form-36 (SF-36) 설문지 작성을 시행하였다. 두 목 장애 설문지는 SF-36과 탈출된 디스크의 위치, 디스크 높이, 척수관 내 디스크의 비율, 척수의신호 강도 변화, 구상 관절의 골극 존재 여부를 포함한 영상학적 소견과의 상관관계를 비교하였다. 두 설문지의 비교를 위해 스피어만 상관 분석을 수행하였다. 결과: 본 연구에는 평균 연령 43.2세인 82명의 DCDD 환자가 포함되었다. 두 설문지들 모두 SF-36과의 중등도 이상의 상관관계를 보였으며, NPDS가NDI보다 SF-36과 더 강한 상관관계를 보였다. 설문지들은 탈출된 디스크의 비율과 중간 정도의 상관관계를 보였으며 NPDS가 좀 더 높은 상관관계를 보였다. 하지만, 두설문지 모두 연령, 성별, 체질량 지수, 탈출된 디스크의 위치, 디스크 높이와는 상관관계가 관찰되지 않았다. 결론: NDI와 NPDS 모두 훌륭한 목 장애 평가 도구이다. 그러나 본 연구에서 단일 레벨 DCDD 환자를 대상으로 실시한 결과 NPDS가 NDI보다 조금 더우수한 평가 지표로 생각된다. 약칭 제목: 퇴행성 경추 디스크 질환에 대한 한국판 목 장애 설문지의 비교 Study Design: A prospective study. Objectives: This study aimed to validate the outcomes of two Korean-language questionnaires on neck disability by conducting a comparative analysis with radiological findings and quality of life scores. Summary of Literature Review: Numerous studies have been conducted on both neck disability questionnaires; however, no studies have yet compared both simultaneously. Materials and Methods: Patients with degenerative cervical disc disease (DCDD) completed the Korean versions of the Neck Disability Index (NDI) and the Neck Pain and Disability Scale (NPDS), as well as the Short Form-36 (SF-36). The neck disability questionnaires were compared to the SF-36 and radiographic findings, including the level of the herniated intervertebral disc (HIVD), disc height, the percentage of the HIVD in the spinal canal, the presence of signal intensity changes in the spinal cord, and the presence of a bony spur in the uncovertebral joint. Spearman correlation analysis was performed to compare the two surveys. Results: This study included 82 DCDD patients with a mean age of 43.2 years. Both questionnaires demonstrated a moderate to strong correlation with the SF-36, with the NPDS showing a stronger correlation than the NDI. Both questionnaires exhibited a moderate correlation with the percentage of the HIVD, and the NPDS showed a slightly higher correlation. However, no correlation was observed between either questionnaire and age, sex, body mass index, the level of the HIVD, or disc height. Conclusions: Both the NDI and NPDS are excellent tools for evaluating neck disorders. However, based on this study, the NPDS appears to be a slightly better assessment tool than the NDI.

Functional Expression of yeast NDI1 Gene in the Mouse Liver Hepatocytes

Byoung Boo Seo,Hae-Bum Song 한국동물생명공학회(구 한국동물번식학회) 2011 발생공학 국제심포지엄 및 학술대회 Vol.2011 No.1

Mitochondria diseases have been reported to involve structural and functional defects of complex I-V. Especially, many of these diseases are known to be related to dysfunction of mitochondrial proton-translocating NADH-ubiquinone oxidoreductase (complex I). The dysfunction of mitochondria complex I is associated with neurodegenerative disorders, such as Parkinson's disease, Huntington's disease, and Leber’s hereditary optic neuropathy (LHON). Mammalian mitochondrial proton-translocating NADH–quinone oxidoreductase (complex I) is largest and consists of at least 46 different subunits. In contrast, the NDI1 gene of is a single subunit rotenone-insensitive NADH-quinone oxidoreductase that is located on the matrix side of the inner mitochondrial membrane. The gene using a recombinant adeno-associated virus vector (rAAV-NDI1) was successfully expressed in AML12 mouse liver hepatocytes. The NDI1-transduced cells were able to grow in media containing rotenone. In contrast, control cells that did not receive the gene failed to survive. The expressed Ndi1 enzyme was recognized to be localized in mitochondria by confocal immunofluorescence microscopic analyses and immunoblotting. Using digitonin-permeabilized cells, it was shown that the NADH oxidase activity of the NDI1-transduced cells was not affected by rotenone which is inhibitor of complex I, but was inhibited by antimycin A. Furthermore, these results shown that Ndi1 can be functionally expressed in the AML12 mouse liver hepatocytes. It is conceivable that the gene is powerful tool for gene therapy of mitochondrial diseases caused by complex I deficiency. In the future, I will attempt to functionally express the NDI1 gene in mouse embryonic stem (mES) cell.

Naphthalene-Diimide-Based Small Molecule Containing a Thienothiophene Linker for n-Type Organic Field-Effect Transistors

이경석,오종규,서의현,이규민,유은애,안태규,장재영,김윤희 한국고분자학회 2022 Macromolecular Research Vol.30 No.7

A naphthalene diimide (NDI)-based small molecule with a thienothiophene linker (NDI-TT-NDI) was synthesized for use as a semiconductor layer in solutionprocessable n-type organic field-effect transistors (OFETs). The thienothiophene linker was introduced to the donor site between the two NDIs to impart planarity to the molecular backbone, which is favorable for inducing high crystallinity, and the morphological and crystal characteristics of the resulting film were analyzed. An additional annealing treatment applied to the NDT-TT-NDI films changed their orientation such that the molecular ordering and crystallinity of the film were significantly improved at a specific annealing temperature. The optimally annealed NDI-TT-NDI film exhibited a distinct edge-on molecular orientation with a narrow intermolecular π-π stacking distance, which is advantageous for lateral charge transport along the stacks. Consequently, an optimally annealed NDI-TT-NDI-based OFET exhibited electron mobilities of up to 0.032 cm2V-1s-1 and an on/off ratio of 1.0 × 107.

Mitochondrial Complex I as a Possible Modulator of Tumorigenesis and Progression in Breast Cancer

Byoung B Seo,Antonio F Santidrian,Zae Young Ryoo,Hum Dae Park 한국동물번식학회 2012 Reproductive & Developmental Biology(Supplement) Vol.36 No.2s

Tumor cells express altered metabolic activities often linked to mitochondrial dysfunction. Such mitochondrial defects can inhibit oxidative phosphorylation, change the cellular redox status (NAD+/NADH), increase production of reactive oxygen species (ROS), and cause DNA damage that further supports tumorigenesis and a metastatic phenotype1,2. Mitochondrial Complex I (NADH dehydrogenase) is a major site of ROS production in mitochondria and regulator of the NAD+/NADH ratio. This study is focused on mitochondrial complex I as a possible modulator of tumorigenesis and progression in breast cancer. We used NADH dehydrogenase from yeast, called NDI1, to augment complexI activity in metastatic human breast cancer cells. We followed NDI1 functionality and impact on tumor cell behavior in vitro and tumor progression in vivo. Augmentation of NADH dehydrogenase activity through NDI1 resulted in an enhanced NAD+/NADH ratio and slight inhibition of ROS production. Importantly, NDI1 expression inhibited metastasis and tumor growth in the mammary fad pad of immune deficient mice, as seen by non-invasive bioluminescence imaging and histology. The mechanisms involve NDI1-induced inhibition of the AKT/mTOR survival pathway and autophagy stimulation. Knock-down of ATG5 partially reversed the anti-metastatic effect of NDI1, demonstrating that enhancement of autophagy is responsible for NDI1-mediated inhibition of breast cancer spreading. The results indicate that mitochondrial complex I activity can drastically impact tumorigenesis and metastasis in breast cancer, and that augmentation of complex I function through NDI1 can inhibit tumor formation and cancer progression through NAD+/NADH ratio modulation.

레이저 피닝한 Ni 12% STS316L 피로특성의 신뢰성 향상

이금화(Gum-Hwa Lee),구경희(Kyoung-Hee Gu),남기우(Ki-Woo Nam) 대한기계학회 2022 大韓機械學會論文集A Vol.46 No.6

수소자동차는 환경문제 해결을 위하여 주목받고 있다. 그러나 수소 저장 탱크의 재료에 관한 안전성 및 신뢰성에 관한 연구가 거의 없다. 본 연구는 수소저장 탱크의 배관 재료 Ni 12% STS316L강의 안전성 및 신뢰성을 확보하기 위한 것이다. Non-LP 및 LP 평활시험편의 피로한도를 결정하고, LP한 균열형 상비(As) 0.1~1.0의 무해한 균열 깊이(a<SUB>hml</SUB>)를 평가하였다. 또한, a<SUB>hml</SUB>은 As, 피로한도를 감소시키는 균열 깊이(a<SUB>25</SUB>, a<SUB>50</SUB>) 및 NDI에서 검출가능한 균열 깊이(aNDI)와 비교하였다. 균열 무해화조건은 모두 균열최심점(A점)에서 결정되었다. a<SUB>hml</SUB>은 0.418~0.539 mm이고, 이 값은 긴 균열의 K<SUB>th(l)</SUB>로 평가 가능하였다. a<SUB>hml</SUB> 은 균열형상비(As)에 크게 의존하지 않았다. NDI 후에 검출한 균열을 보수 후 피닝하지 않는 경우, 균열검출 확율이 매우 높은 NDI1로 실시할 필요가 있다. Hydrogen vehicles are attracting attention to solve environmental problems. However, few studies exist on the safety and reliability of materials for hydrogen storage tanks. This study aims to secure the safety and reliability of Ni12% STS316L steel, a piping material for hydrogen storage tanks. The fatigue limits of non-LP and LP smooth specimens were determined, and the harmless crack depth (a<SUB>hml</SUB>) of the crack aspect ratio (As) 0.1~1.0 via the LP was evaluated. In addition, a<SUB>hml</SUB> was compared with As, the crack depth that reduces the fatigue limit (a<SUB>25</SUB>, a<SUB>50</SUB>), and the crack depth (a<SUB>NDI</SUB>) detectable in NDI. All crack harmless conditions were determined at the crack deepest point (point A). a<SUB>hml</SUB> is 0.418~0.539 mm, and this value can be evaluated as K<SUB>th(l)</SUB> of a long crack. a<SUB>hml</SUB> did not significantly depend on As. If the crack detected after NDI is not peened after repair, then NDI1, which has a very high crack detection probability, must be performed.

Functional Expression of Saccharomyces cerevisiae NADH-quinone Oxidoreductase (NDI1) Gene in the AML12 Mouse Liver Hepatocytes for the Applying Embryonic Stem Cell

Byoung Boo Seo,Humdai Park 한국동물번식학회 2011 Reproductive & developmental biology Vol.35 No.4