1,4,5,8-Naphthalenetetracarboxylic dianhydride(NTDA) - ≥96% , CAS No.81-30-1

CAS: 81-30-1 Cat. No.: N107577 Peso molecular: 268.18 Beilstein Registry Number: 272788 Número EC: 201-342-5

GRADE & PURITY ≥96%

Synonyms

NTCDA | AKOS003614689 | 1,8:4, 5-Naphthalenetetracarboxylic dianhydride | Isochromeno[6,5,4-def]isochromene-1,3,6,8-tetraone | N0755 | Naphthalene-1,8:4,5-tetracarboxylic dianhydride | NCGC00357221-01 | NSC 84241 | 1,4,5,8-naphthalenetetracarboxylic-1,8:4

Storage

Room temperature,Argon charged

Shipped In

Normal

Descripción general

1,4,5,8-Naphthalenetetracarboxylic dianhydride (NTCDA) is a tetrafunctional monomer that can be used as an electron transporting material in organic electronics

Specifications

Sinónimos

NTCDA | AKOS003614689 | 1, 8:4, 5-Naphthalenetetracarboxylic dianhydride | Isochromeno[6, 5, 4-def]isochromene-1, 3, 6, 8-tetraone | N0755 | Naphthalene-1, 8:4, 5-tetracarboxylic dianhydride | NCGC00357221-01 | NSC 84241 | 1, 4, 5, 8-naphthalenetetracarboxylic-1, 8:4

Especificaciones y pureza

≥96%

Condiciones de almacenamiento de almacenamiento

Room temperature, Argon charged

Enviado en

Normal

Pureza

≥96%

Nombres e identificadores

• Pubchem Sid: 504751153
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504751153
• Sonrisas canónicas: C1=CC2=C3C(=CC=C4C3=C1C(=O)OC4=O)C(=O)OC2=O
• IUPAC Name: 6,13-dioxatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaene-5,7,12,14-tetrone
• InChIKey: YTVNOVQHSGMMOV-UHFFFAOYSA-N
• INCHI: 1S/C14H4O6/c15-11-5-1-2-6-10-8(14(18)20-12(6)16)4-3-7(9(5)10)13(17)19-11/h1-4H
• Isómeros SMILES: C1=CC2=C3C(=CC=C4C3=C1C(=O)OC4=O)C(=O)OC2=O
• WGK Alemania: 2
• RTECS: QK3695000
• Peso molecular: 268.18
• Beilstein: 272788
• Reaxy-Rn: 272788
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=272788&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Clase Isocoumarins and derivatives

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Clase: Isocoumarins and derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Isocoumarins and derivatives
• Alternative Parents: Naphthalenes 2-benzopyrans Pyranones and derivatives Heteroaromatic compounds Lactones Oxacyclic compounds Organooxygen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Isocoumarin - Benzopyran - Naphthalene - 2-benzopyran - Pyranone - Benzenoid - Pyran - Heteroaromatic compound - Lactone - Oxacycle - Organoheterocyclic compound - Organic oxygen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Aromatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as isocoumarins and derivatives. These are polycyclic compounds containing an isochromane which bears a ketone at the carbon C1.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Propiedades químicas y físicas

• Sensibilidad: Moisture Sensitive
• Punto de fusión (°C): >300℃
• Peso molecular: 268.180 g/mol
• XLogP3: 1.900
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 268.001 Da
• Monoisotopic Mass: 268.001 Da
• Topological Polar Surface Area: 86.700 Ų
• Heavy Atom Count: 20
• Formal Charge: 0
• Complexity: 446.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Referencias

1. Linhong Liao, Xiao Lin, Jie Zhang, Zhiyuan Hu, Fengshou Wu.  (2023)  Facile preparation of carbon dots with multicolor emission for fluorescence detection of ascorbic acid, glutathione and moisture content.  JOURNAL OF LUMINESCENCE,      [PMID:] [10.1016/j.jlumin.2023.120169]

2. Yanqing Cong, Xinyue Li, Shiyi Zhang, Qiuang Zheng, Yi Zhang, Shi-Wen Lv.  (2023)  Embedding Carbon Quantum Dots into Crystalline Polyimide Covalent Organic Frameworks to Enhance Water Oxidation for Achieving Dual-Channel Photocatalytic H2O2 Generation in a Wide pH Range.  ACS Applied Materials & Interfaces,      [PMID:37672480] [10.1021/acsami.3c09039]

3. Liao Linhong, Lin Xiao, Wang Kai, Hu Zhiyuan, Wu Fengshou.  (2023)  Highly luminescent nitrogen and sulfur co-doped carbon dots for Sn2+ and S2− sensing and dual-mode anti-counterfeiting.  MICROCHIMICA ACTA,  190  (8): (1-11).  [PMID:37507622] [10.1007/s00604-023-05922-9]

4. Hui Ling, Ziting Zhen, Yuhang Sun, Gang Li, Chao Wang, Xiaoping Yang.  (2023)  Enhancement of interfacial properties of HMCF composites by constructing of rigid-flexible interphase through naphthalenediimide with different flexible chain lengths.  POLYMER COMPOSITES,  44  (9): (6149-6163).  [PMID:] [10.1002/pc.27553]

5. Meichen Guo, Wu Tang, Chenbin Tang, Xuesong He, Jiahui Hu, Cong Fan.  (2023)  Small-Molecule Organic Cathodes with Carbon Coating for Highly Efficient Potassium-ion Batteries.  ChemSusChem,  16  (15): (e202300343).  [PMID:37013264] [10.1002/cssc.202300343]

6. Le Cheng, Tinghao Ma, Binghao Zhang, Libei Huang, Weihua Guo, Feijun Hu, He Zhu, Zhaoyu Wang, Tingting Zheng, Deng-Tao Yang, Chi-Kit Siu, Qi Liu, Yang Ren, Chuan Xia, Ben Zhong Tang, Ruquan Ye.  (2022)  Steering the Topological Defects in Amorphous Laser-Induced Graphene for Direct Nitrate-to-Ammonia Electroreduction.  ACS Catalysis,      [PMID:] [10.1021/acscatal.2c03219]

7. Gao Jingqing, Liu Xiaobang, Ren Peng, Gao Jianlei, Chen Yong, Chen Zhijun.  (2022)  Removal behavior and mechanism of amino/carboxylate-functionalized Fe@SiO2 for Cr(VI) and Cd(II) from aqueous solutions.  ENVIRONMENTAL SCIENCE AND POLLUTION RESEARCH,  29  (47): (72058-72073).  [PMID:35610446] [10.1007/s11356-022-20048-w]

8. Di Liu, Yunning Chen, Renquan Guan, Jie Zhao, Huimin Jin, Siyi Zhang, Qingkun Shang.  (2022)  Photocatalytic performance of heterojunction S-Tyr-NDI-Tyr/TiO2 formed by self-assembled naphthalimide derivatives and titanium dioxide.  CHEMOSPHERE,      [PMID:35183575] [10.1016/j.chemosphere.2022.134046]

9. Wei Li, Yanhong Li, Jürgen Caro, Aisheng Huang.  (2021)  Fabrication of a flexible hydrogen-bonded organic framework based mixed matrix membrane for hydrogen separation.  JOURNAL OF MEMBRANE SCIENCE,      [PMID:] [10.1016/j.memsci.2021.120021]

10. Minhui Zheng, Zhoulu Wang, Qiang Ru, Haikuo Fu, Jun Zhang, Zikang Pan, Jiaqi Wang, Qizhen Xie, Xing Zhao.  (2021)  NASICON type KTi2(PO4)3 decorated by NTCDA-derived carbon layer for enhanced lithium/sodium storage.  JOURNAL OF COLLOID AND INTERFACE SCIENCE,      [PMID:34689047] [10.1016/j.jcis.2021.10.009]

11. Lihong Tao, Jianjun Zhao, Jun Chen, Caixia Ou, Weixia Lv, Shengwen Zhong.  (2021)  1,4,5,8-Naphthalenetetracarboxylic dianhydride grafted phthalocyanine macromolecules as an anode material for lithium ion batteries.  Nanoscale Advances,  3  (11): (3199-3215).  [PMID:36133650] [10.1039/D1NA00115A]

12. Liu Xufei, Qiu Shengqiang, Mei Peng, Zhang Qing, Yang Yingkui.  (2020)  Chain structure-dependent electrochemical performance of polyimide cathode materials for lithium-ion batteries.  JOURNAL OF MATERIALS SCIENCE,  56  (5): (3900-3910).  [PMID:] [10.1007/s10853-020-05510-9]

13. Kai Hu, Jingyi Qiao, Weixia Zhu, Xiaohui Chen, Chunhong Dong.  (2019)  Magnetic naphthalene-based polyimide polymer for extraction of Sudan dyes in chili sauce.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2019.104073]

14. Kaixiang Shi, Hongyan Yao, Yongcun Zou, Yanfeng Wei, Ningning Song, Shuai Zhang, Ye Tian, Shiyang Zhu, Bo Zhang, Shaowei Guan.  (2019)  Crosslinked porphyrin-based polyimides: Tunable porosity parameters and carbon dioxide adsorption.  MICROPOROUS AND MESOPOROUS MATERIALS,      [PMID:] [10.1016/j.micromeso.2019.06.016]

15. Ying Zhang, Ronglan Zhang, Fei Yang, Jianshe Zhao.  (2017)  Binuclear Metal Phthalocyanines Catalysis for Li/SOCl2 Batteries: An Experimental and Computational Study.  Energy Technology,  6  (7): (1342-1351).  [PMID:] [10.1002/ente.201700929]

16. Ting Wang, Rui Xue, Huiqin Chen, Peiling Shi, Xi Lei, Yuli Wei, Hao Guo, Wu Yang.  (2017)  Preparation of two new polyimide bond linked porous covalent organic frameworks and their fluorescence sensing application for sensitive and selective determination of Fe3+.  NEW JOURNAL OF CHEMISTRY,  41  (23): (14272-14278).  [PMID:] [10.1039/C7NJ02134H]

17. Lihua Ma, Song Guo, Jifu Sun, Caishun Zhang, Jianzhang Zhao, Huimin Guo.  (2013)  Green light-excitable naphthalenediimide acetylide-containing cyclometalated Ir(III) complex with long-lived triplet excited states as triplet photosensitizers for triplet–triplet annihilation upconversion.  DALTON TRANSACTIONS,  42  (18): (6478-6488).  [PMID:23471114] [10.1039/C3DT32815E]

18. Shaozhong Zeng, Limin Guo, Fangming Cui, Zhe Gao, Jian Zhou, Jianlin Shi.  (2010)  In situ Self-Assembly of Zigzag Polyimide Chains to Crystalline Branched Supramolecular Structures with High Surface Area.  MACROMOLECULAR CHEMISTRY AND PHYSICS,  211  (6): (698-705).  [PMID:] [10.1002/macp.200900506]

19. Zhen Deng, Long Ma, Gang Li, Yunhua Yu, Xiaoping Yang.  (2024)  Alleviating interfacial thermal residual stress of carbon fiber-reinforced composites by molecular pulley effect of aldehyde-functionalized polyrotaxane.  COMPOSITES COMMUNICATIONS,      [PMID:] [10.1016/j.coco.2024.102146]

20. Junbo Chen, Yuanpeng Xie, Maosong Tian, Jingfu Tian, Zhihao Liang, Haibo Xie, Menglan Lv.  (2025)  Cellulose-derived hydrogel with low vaporization enthalpy enables highly efficient solar steam generation.  CARBOHYDRATE POLYMERS,      [PMID:40049964] [10.1016/j.carbpol.2025.123385]

21. Lingwei Li, Jiale Zhao, Yijiao Zhang, Yao Wang, Yanming Wang, Bihai Su, Feibo Li, Linlin Shi, Ping Li, Zhixiao Zhang, Xiaoliang Zhang, Jingbo Mu, Yu Dong.  (2024)  Construction of proton exchange membrane with high proton conductivity based on 3D self-assembly structures as multiple proton transport channels.  INTERNATIONAL JOURNAL OF HYDROGEN ENERGY,      [PMID:] [10.1016/j.ijhydene.2024.11.355]

22. Hongyang Wang, Bo Zhao, Rui Dong, Ping Wen, Mingjin Fan.  (2024)  Covalent-Organic Framework Nanomaterials: Energy Band Engineering Generating Ultrathin Lubrication Films for Excellent Lubrication.  ACS Applied Materials & Interfaces,      [PMID:39239968] [10.1021/acsami.4c11808]

23. Haolin Xie, Qingqing Qiu, Huan Li, Ping Liu, Putrakumar Balla, Xiaopeng Qi, Tongxiang Liang, Jinming Zeng.  (2024)  Directly Grown Polyimide Covalent Organic Framework Films with High Electrochromic and Energy-Storage Performance.  ACS Applied Materials & Interfaces,      [PMID:39698745] [10.1021/acsami.4c16702]

24. Rong Ji, Yuming Dong, Xinyu Sun, Chengsi Pan, Yunfan Yang, Hui Zhao, Yongfa Zhu.  (2024)  Efficient H2O2 photocatalysis by a novel organic semiconductor with electron donor-acceptor interface.  APPLIED CATALYSIS B-ENVIRONMENTAL,      [PMID:] [10.1016/j.apcatb.2024.123884]

25. Miao Cao, Yulang Qiu, Man Yang, Yanyan Zhang, Qiange Li, Shishen Zhang, Peng Li, Qi Sui.  (2024)  Electron-deficient naphthalenediimides modified g-C3N4 for boosting photocatalytic hydrogen evolution in freshwater and seawater.  INTERNATIONAL JOURNAL OF HYDROGEN ENERGY,      [PMID:] [10.1016/j.ijhydene.2024.11.439]

26. Shuyang Zhou, Hang Zhao, Na Zhang, Lei Yin, Jinbo Bai.  (2024)  Improved high-temperature energy storage performance of sandwich PEI-based composites via introducing charge traps by differential functional fillers.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2024.158941]

27. Junlei Liu, Shenglian Yao, Weiwei Hou, Dianyu Tang, Wentao Chi, Yusheng Chen, Yihu Liu, Zhenliang Zhang, Mi Ouyang, Cheng Zhang.  (2024)  Preparation of Positive and Negative Composite Electrode Materials for High-Performance Aqueous Asymmetric Supercapacitor by a Sequential Two-Step Reaction.  ACS Applied Energy Materials,      [PMID:] [10.1021/acsaem.4c00762]

28. Zewan Qin, Qing Guan, Yating Lu, Yu Tian, Xia Yang.  (2024)  The design and preparation of NDI modified MOFs for high efficiency removal of MB and Cr(VI).  Journal of Environmental Chemical Engineering,      [PMID:] [10.1016/j.jece.2024.112740]

29. Tao Wang, Mengyu Zhang, Rui Song, Zhenhao Fan, Ahmad Azmin Mohamad, Kaixin Song, Dawei Wang, Mingfu Zhang.  (2025)  Ultrahigh Energy Density in All-Organic Composites Synergistically Tailored by PMMA and Molecular Semiconductor.  ADVANCED FUNCTIONAL MATERIALS,      [PMID:] [10.1002/adfm.202422652]

30. Peiwen Yang, Weijie Kong, Bo Li, Siyun Liang, Yuchen Qu, Peiluo Shi, Gang Li, Xiaoping Yang.  (2025)  Enhanced thermal conductive and interfacial performance of M40X carbon fiber/epoxy composites with multi-dimensional liquid crystalline interphase: A combined method of experimental analysis and molecular simulation.  COMPOSITES PART B-ENGINEERING,      [PMID:] [10.1016/j.compositesb.2025.112866]

31. Zhengdong Wang, Chenxin Liu, Xiaolong Cao, Bin Cheng, Jinkai Wang, Guotai Sun.  (2025)  Molecularly Ordered Epoxy/Organic Acceptor Composites for Superior Thermal Transport and Electrical Insulation Performance.  ADVANCED FUNCTIONAL MATERIALS,      [PMID:] [10.1002/adfm.202516105]

32. Jinyang Peng, Xinran Zhao, Yuxi Huang, Cuijiao Zhao, Jun Yang, Minjie Shi.  (2025)  Electron-Delocalized Benzimidazole-Linked Organic Electrode with Enhanced Redox Availability for High-Performance Ammonium Capture via Capacitive Deionization.  ADVANCED FUNCTIONAL MATERIALS,      [PMID:] [10.1002/adfm.202506369]

33. Zhen Deng, Peiwen Yang, Long Ma, Gang Li, Yunhua Yu, Xiaoping Yang.  (2025)  Constructing interfacial pulleys with branched polynaphthalamic acid polyrotaxane: a new route to superior interfacial toughness and strength in carbon fiber-reinforced composites.  COMPOSITES PART B-ENGINEERING,      [PMID:] [10.1016/j.compositesb.2025.112597]

34. Hui Zhang, Zhi Xiang, Pengcheng Fang, Shuhuan Zang, Zhengzhi Zheng.  (2025)  Soluble Polyimide-Modified Epoxy Resin With Enhanced Comprehensive Performances.  JOURNAL OF APPLIED POLYMER SCIENCE,      [PMID:] [10.1002/app.57400]

35. Chuying Zhang, Haotong Guo, Na Zhang, Liming Jin, Jinbo Bai, Hang Zhao.  (2025)  Improved Electromechanical Performance of Dielectric Elastomers via Constructing an All-Organic Composite Structure.  MACROMOLECULES,      [PMID:] [10.1021/acs.macromol.5c00971]

36. Cao Jueran, Huang Enlin, Zhong Ziting, Jiang Tingjie, Zhang Haoran, Li Wei, Zhang Xuejie, Hu Chaofan, Lei Bingfu.  (2025)  Dual-mode photochromic luminescence of carbon dots induced by photoinduced electron transfer.  Science China-Materials,      [PMID:] [10.1007/s40843-025-3555-y]

37. Nana Li, Hao Shen, Mengdi Hao, Wanqiu Huang, Ying Han, Fan Yang, Shaoning Yu.  (2025)  Self-assembling heterostructured MOF@HOF nanozyme for ultrasensitive α-amylase activity detection.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2025.115830]

38. Hailiang Yang, Qian Chen, Yuankui Huang, Yaoping Hu.  (2025)  Carbon nitride quantum dots with full-color room-temperature phosphorescence via in situ precursor engineering and rigid matrix confinement.  CARBON,      [PMID:] [10.1016/j.carbon.2025.121074]

39. Yuqi Li, Yikai Chen, Ziting Zhong, Zhun Ran, Shihuan Luo, Zhenzhen Li, Yong Shao, Jianle Zhuang, Xuejie Zhang, Zhouyi Guo, Yingliang Liu, Zhiming Liu, Chaofan Hu.  (2025)  Surface-Functionalized Carbon Dots with Photochromic Luminescence in Water and PVA Film.  Laser & Photonics Reviews,      [PMID:] [10.1002/lpor.202501947]

40. Peipei Zhang, Haoran Xu, Jun Yang, Minjie Shi, Yuqing Lin.  (2025)  High-efficiency electrochemical desalination enabled by nanosheet-structured redox polymer for sustainable and versatile water treatment.  WATER RESEARCH,      [PMID:40245802] [10.1016/j.watres.2025.123646]

41. Qiang Li, Lingxuan Yang, Qi Zhou, Erpeng Wang, Yuhao Lin, Hao Du, Zhiheng Li, Limin Jin, Chuncheng Chen, Qi Wang.  (2026)  Sustained hydroxyl radical generation via a robust metal-free polyimide photocatalyst for water remediation.  APPLIED CATALYSIS B-ENVIRONMENTAL,      [PMID:] [10.1016/j.apcatb.2026.126390]

42. Haolin Xie, Jinming Zeng, Zheng Xie, Yang Ou, Qingqing Qiu, Huan Li, Huiling Liu, Balla Putrakumr, Junyi Wu, Ping Liu, Tongxiang Liang.  (2026)  Extending the π-Conjugated Benzoimidazoisoindolone-based n-Type Ladder Polymers: Highly Air-robust Aqueous Sodium-ion Electrochromic Energy Storage and Mechanism.  Materials Horizons,      [PMID:41575467] [10.1039/D5MH01972A]

43. Chen Chuanli, Yang Yuezhen, Zhang Lutong, Dai Wenbo, Lei Yunxiang, Liu Miaochang, Wu Huayue, Huang Xiaobo, Yan Dongpeng.  (2026)  Multiple hydrogen bonding enables large-area doped phosphorescent glasses with robust stability and high-temperature afterglow.  Nature Communications,      [PMID:41547867] [10.1038/s41467-026-68590-2]

44. Yuxin Song, Rong Guo, Jianming Zhong, Xu Zhang, Fuchang Shu, Yongbing Zhuang.  (2026)  Effects of Repeat Unit Sequences on Physical and Gas transport Properties of Soluble Copolyimides.  POLYMER,      [PMID:] [10.1016/j.polymer.2026.129619]

45. Cheng Wang, Luyao Li, Weicun Chu, Zhongliang Dong, Yinlong Zhu, Xiaoming Zhao, Lixiong Yin, Riming Nie, Wanlin Guo.  (2026)  Thermally triggered polymer interface engineering for efficient and stable air-processed perovskite solar cells.  Journal of Energy Chemistry,      [PMID:] [10.1016/j.jechem.2026.02.033]