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Title: Hollow organic capsules assemble into cellular semiconductors

Abstract

Self-assembly of electroactive molecules is a promising route to new types of functional semiconductors. Here we report a capsule-shaped molecule that assembles itself into a cellular semiconducting material. The interior space of the capsule with a volume of ~415 Å3 is a nanoenvironment that can accommodate a guest. To self-assemble these capsules into electronic materials, we functionalize the thiophene rings with bromines, which encode self-assembly into two-dimensional layers held together through halogen bonding interactions. In the solid state and in films, these two-dimensional layers assemble into the three-dimensional crystalline structure. This hollow material is able to form the active layer in field effect transistor devices. We find that the current of these devices has strong response to the guest’s interaction within the hollow spaces in the film. These devices are remarkable in their ability to distinguish, through their electrical response, between small differences in the guest.

Authors:
 [1]; ORCiD logo [2];  [1];  [1];  [3];  [4]; ORCiD logo [5];  [1];  [1]; ORCiD logo [6]
  1. Columbia Univ., New York, NY (United States). Dept. of Chemistry
  2. Columbia Univ., New York, NY (United States). Dept. of Chemistry. Columbia Nano Initiative
  3. Columbia Univ., New York, NY (United States). Dept. of Applied Physics and Applied Mathematics
  4. Columbia Univ., New York, NY (United States). Columbia Nano Initiative
  5. Columbia Univ., New York, NY (United States). Dept. of Applied Physics and Applied Mathematics; Brookhaven National Lab. (BNL), Upton, NY (United States). Condensed Matter Physics and Materials Science Dept.
  6. Columbia Univ., New York, NY (United States). Dept. of Chemistry; Wuhan Univ. of Science and Technology (China). The State Key Lab. of Refractories and Metallurgy. Inst. of Advanced Materials and Nanotechnology. School of Chemistry and Chemical Engineering
Publication Date:
Research Org.:
Columbia Univ., New York, NY (United States); Brookhaven National Lab. (BNL), Upton, NY (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22); National Science Foundation (NSF)
OSTI Identifier:
1499954
Grant/Contract Number:  
FG02-01ER15264; SC0012704; DMR-1420634
Resource Type:
Accepted Manuscript
Journal Name:
Nature Communications
Additional Journal Information:
Journal Volume: 9; Journal ID: ISSN 2041-1723
Publisher:
Nature Publishing Group
Country of Publication:
United States
Language:
English
Subject:
36 MATERIALS SCIENCE; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; electronic materials; molecular capsules; organic chemistry; self-assembly

Citation Formats

Zhang, Boyuan, Hernández Sánchez, Raúl, Zhong, Yu, Ball, Melissa, Terban, Maxwell W., Paley, Daniel, Billinge, Simon J. L., Ng, Fay, Steigerwald, Michael L., and Nuckolls, Colin. Hollow organic capsules assemble into cellular semiconductors. United States: N. p., 2018. Web. doi:10.1038/s41467-018-04246-0.
Zhang, Boyuan, Hernández Sánchez, Raúl, Zhong, Yu, Ball, Melissa, Terban, Maxwell W., Paley, Daniel, Billinge, Simon J. L., Ng, Fay, Steigerwald, Michael L., & Nuckolls, Colin. Hollow organic capsules assemble into cellular semiconductors. United States. doi:10.1038/s41467-018-04246-0.
Zhang, Boyuan, Hernández Sánchez, Raúl, Zhong, Yu, Ball, Melissa, Terban, Maxwell W., Paley, Daniel, Billinge, Simon J. L., Ng, Fay, Steigerwald, Michael L., and Nuckolls, Colin. Wed . "Hollow organic capsules assemble into cellular semiconductors". United States. doi:10.1038/s41467-018-04246-0. https://www.osti.gov/servlets/purl/1499954.
@article{osti_1499954,
title = {Hollow organic capsules assemble into cellular semiconductors},
author = {Zhang, Boyuan and Hernández Sánchez, Raúl and Zhong, Yu and Ball, Melissa and Terban, Maxwell W. and Paley, Daniel and Billinge, Simon J. L. and Ng, Fay and Steigerwald, Michael L. and Nuckolls, Colin},
abstractNote = {Self-assembly of electroactive molecules is a promising route to new types of functional semiconductors. Here we report a capsule-shaped molecule that assembles itself into a cellular semiconducting material. The interior space of the capsule with a volume of ~415 Å3 is a nanoenvironment that can accommodate a guest. To self-assemble these capsules into electronic materials, we functionalize the thiophene rings with bromines, which encode self-assembly into two-dimensional layers held together through halogen bonding interactions. In the solid state and in films, these two-dimensional layers assemble into the three-dimensional crystalline structure. This hollow material is able to form the active layer in field effect transistor devices. We find that the current of these devices has strong response to the guest’s interaction within the hollow spaces in the film. These devices are remarkable in their ability to distinguish, through their electrical response, between small differences in the guest.},
doi = {10.1038/s41467-018-04246-0},
journal = {Nature Communications},
number = ,
volume = 9,
place = {United States},
year = {2018},
month = {5}
}

Journal Article:
Free Publicly Available Full Text
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Citation Metrics:
Cited by: 8 works
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Figures / Tables:

Fig. 1 Fig. 1 : Structures of cellular semiconductors. a Trimer 1; and b 1-Br12. Van der Waals Surface of 1-Br12 seen from the side (c), and top (f). In the sequence c-e and f–h the molecule is trimmed down to expose its cavity or capsule

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Works referenced in this record:

Synthesis, Properties, and Design Principles of Donor–Acceptor Nanohoops
journal, September 2015


Highly Sensitive NH 3 Detection Based on Organic Field-Effect Transistors with Tris(pentafluorophenyl)borane as Receptor
journal, September 2012

  • Huang, Weiguo; Besar, Kalpana; LeCover, Rachel
  • Journal of the American Chemical Society, Vol. 134, Issue 36
  • DOI: 10.1021/ja305287p

Electronic sensing of vapors with organic transistors
journal, April 2001

  • Crone, B.; Dodabalapur, A.; Gelperin, A.
  • Applied Physics Letters, Vol. 78, Issue 15
  • DOI: 10.1063/1.1360785

Theory of gas-diffusion controlled sensitivity for thin film semiconductor gas sensor
journal, November 2001


Response characteristics of lead phthalocyanine gas sensor: effects of film thickness and crystal morphology
journal, June 1998


Thiophene-Based, Radial π-Conjugation: Synthesis, Structure, and Photophysical Properties of Cyclo-1,4-phenylene-2′,5′-thienylenes
journal, November 2014

  • Ito, Hideto; Mitamura, Yukari; Segawa, Yasutomo
  • Angewandte Chemie International Edition, Vol. 54, Issue 1
  • DOI: 10.1002/anie.201409389

Concise Synthesis and Crystal Structure of [12]Cycloparaphenylene
journal, March 2011

  • Segawa, Yasutomo; Miyamoto, Shinpei; Omachi, Haruka
  • Angewandte Chemie International Edition, Vol. 50, Issue 14
  • DOI: 10.1002/anie.201007232

Synthesis of Cycloparaphenylenes and Related Carbon Nanorings: A Step toward the Controlled Synthesis of Carbon Nanotubes
journal, May 2012

  • Omachi, Haruka; Segawa, Yasutomo; Itami, Kenichiro
  • Accounts of Chemical Research, Vol. 45, Issue 8
  • DOI: 10.1021/ar300055x

Selective Synthesis and Crystal Structure of [10]Cycloparaphenylene
journal, June 2012

  • Kayahara, Eiichi; Sakamoto, Yoichi; Suzuki, Toshiyasu
  • Organic Letters, Vol. 14, Issue 13
  • DOI: 10.1021/ol301242t

Size-Selective Encapsulation of C60 by [10]Cycloparaphenylene: Formation of the Shortest Fullerene-Peapod
journal, July 2011

  • Iwamoto, Takahiro; Watanabe, Yoshiki; Sadahiro, Tatsuya
  • Angewandte Chemie International Edition, Vol. 50, Issue 36
  • DOI: 10.1002/anie.201102302

[9]Cycloparaphenylene: Nickel-mediated Synthesis and Crystal Structure
journal, April 2011

  • Segawa, Yasutomo; Šenel, Petr; Matsuura, Sanae
  • Chemistry Letters, Vol. 40, Issue 4
  • DOI: 10.1246/cl.2011.423

Characterization of intrinsic hysteresis of pentacene-based organic thin-film transistor through in-situ real-time electrical measurement
journal, January 2014

  • Su, Wei-Cheng; Lee, Chih-Chien; Liu, Shun-Wei
  • Japanese Journal of Applied Physics, Vol. 53, Issue 3S1
  • DOI: 10.7567/JJAP.53.03CC03

Size-selective synthesis of [9]–[11] and [13]cycloparaphenylenes
journal, January 2012

  • Ishii, Yuuki; Nakanishi, Yusuke; Omachi, Haruka
  • Chemical Science, Vol. 3, Issue 7
  • DOI: 10.1039/c2sc20343j

Synthesis and Characterization of [5]Cycloparaphenylene
journal, January 2014

  • Kayahara, Eiichi; Patel, Vijay Kumar; Yamago, Shigeru
  • Journal of the American Chemical Society, Vol. 136, Issue 6
  • DOI: 10.1021/ja413214q

Cyclic 2,12-Porphyrinylene Nanorings as a Porphyrin Analogue of Cycloparaphenylenes
journal, February 2015

  • Jiang, Hua-Wei; Tanaka, Takayuki; Mori, Hirotaka
  • Journal of the American Chemical Society, Vol. 137, Issue 6
  • DOI: 10.1021/ja513102m

Curved Oligophenylenes as Donors in Shape-Persistent Donor-Acceptor Macrocycles with Solvatofluorochromic Properties
journal, July 2015

  • Kuwabara, Takuya; Orii, Jun; Segawa, Yasutomo
  • Angewandte Chemie International Edition, Vol. 54, Issue 33
  • DOI: 10.1002/anie.201503397

Macrocyclization in the Design of Organic n-Type Electronic Materials
journal, September 2016

  • Ball, Melissa; Zhong, Yu; Fowler, Brandon
  • Journal of the American Chemical Society, Vol. 138, Issue 39
  • DOI: 10.1021/jacs.6b05474

A donor–acceptor conjugated block copolymer of poly(arylenevinylene)s by ring-opening metathesis polymerization
journal, January 2015

  • Chang, Shu-Wei; Horie, Masaki
  • Chemical Communications, Vol. 51, Issue 44
  • DOI: 10.1039/C5CC00498E

Strain-Induced Stereoselective Formation of Blue-Emitting Cyclostilbenes
journal, September 2015

  • Chen, Qishui; Trinh, M. Tuan; Paley, Daniel W.
  • Journal of the American Chemical Society, Vol. 137, Issue 38
  • DOI: 10.1021/jacs.5b06258

Atropisomerism in a Belt‐Persistent Nanohoop Molecule: Rotational Restriction Forced by Macrocyclic Ring Strain
journal, March 2012

  • Hitosugi, Shunpei; Nakanishi, Waka; Isobe, Hiroyuki
  • Chemistry – An Asian Journal, Vol. 7, Issue 7
  • DOI: 10.1002/asia.201200187

Belt-Shaped π-Systems: Relating Geometry to Electronic Structure in a Six-Porphyrin Nanoring
journal, November 2011

  • Sprafke, Johannes K.; Kondratuk, Dmitry V.; Wykes, Michael
  • Journal of the American Chemical Society, Vol. 133, Issue 43
  • DOI: 10.1021/ja2045919

Size- and Orientation-Selective Encapsulation of C 70 by Cycloparaphenylenes
journal, September 2013

  • Iwamoto, Takahiro; Watanabe, Yoshiki; Takaya, Hikaru
  • Chemistry - A European Journal, Vol. 19, Issue 42
  • DOI: 10.1002/chem.201302694

Size-Selective Complexation and Extraction of Endohedral Metallofullerenes with Cycloparaphenylene
journal, February 2014

  • Nakanishi, Yusuke; Omachi, Haruka; Matsuura, Sanae
  • Angewandte Chemie International Edition, Vol. 53, Issue 12
  • DOI: 10.1002/anie.201311268

Conjugated Macrocycles: Concepts and Applications
journal, September 2011

  • Iyoda, Masahiko; Yamakawa, Jun; Rahman, M. Jalilur
  • Angewandte Chemie International Edition, Vol. 50, Issue 45
  • DOI: 10.1002/anie.201006198

OLEX2 : a complete structure solution, refinement and analysis program
journal, January 2009

  • Dolomanov, Oleg V.; Bourhis, Luc J.; Gildea, Richard J.
  • Journal of Applied Crystallography, Vol. 42, Issue 2
  • DOI: 10.1107/S0021889808042726

On the degradation of organic field-effect transistors
conference, January 2004

  • Pannemann, Ch.; Diekmann, T.; Hilleringmann, U.
  • Proceedings. The 16th International Conference on Microelectronics, 2004. ICM 2004.
  • DOI: 10.1109/ICM.2004.1434210

Rigid, Conjugated Macrocycles for High Performance Organic Photodetectors
journal, December 2016

  • Zhang, Boyuan; Trinh, M. Tuan; Fowler, Brandon
  • Journal of the American Chemical Society, Vol. 138, Issue 50
  • DOI: 10.1021/jacs.6b10276

Fast Calculation of van der Waals Volume as a Sum of Atomic and Bond Contributions and Its Application to Drug Compounds
journal, September 2003

  • Zhao, Yuan H.; Abraham, Michael H.; Zissimos, Andreas M.
  • The Journal of Organic Chemistry, Vol. 68, Issue 19
  • DOI: 10.1021/jo034808o

Synthesis, Characterization, and Theory of [9]-, [12]-, and [18]Cycloparaphenylene: Carbon Nanohoop Structures
journal, December 2008

  • Jasti, Ramesh; Bhattacharjee, Joydeep; Neaton, Jeffrey B.
  • Journal of the American Chemical Society, Vol. 130, Issue 52
  • DOI: 10.1021/ja807126u

Selective and Random Syntheses of [ n ]Cycloparaphenylenes ( n = 8–13) and Size Dependence of Their Electronic Properties
journal, June 2011

  • Iwamoto, Takahiro; Watanabe, Yoshiki; Sakamoto, Youichi
  • Journal of the American Chemical Society, Vol. 133, Issue 21
  • DOI: 10.1021/ja2020668

Giant Cyclo[ n ]thiophenes with Extended π Conjugation
journal, August 2009

  • Zhang, Fan; Götz, Günther; Winkler, Henrik D. F.
  • Angewandte Chemie International Edition, Vol. 48, Issue 36
  • DOI: 10.1002/anie.200900101

Bottom-up Synthesis and Thread-in-Bead Structures of Finite ( n ,0)-Zigzag Single-Wall Carbon Nanotubes
journal, July 2012

  • Hitosugi, Shunpei; Yamasaki, Takashi; Isobe, Hiroyuki
  • Journal of the American Chemical Society, Vol. 134, Issue 30
  • DOI: 10.1021/ja305723j

Giant Macrocycles Composed of Thiophene, Acetylene, and Ethylene Building Blocks
journal, December 2006

  • Nakao, Kazumi; Nishimura, Masayuki; Tamachi, Tomoya
  • Journal of the American Chemical Society, Vol. 128, Issue 51
  • DOI: 10.1021/ja067077t

Chiral Conjugated Corrals
journal, July 2015

  • Ball, Melissa; Fowler, Brandon; Li, Panpan
  • Journal of the American Chemical Society, Vol. 137, Issue 31
  • DOI: 10.1021/jacs.5b05698

A cyclic octithiophene containing β,β′-linkages
journal, January 2015

  • Asai, Kengo; Fukazawa, Aiko; Yamaguchi, Shigehiro
  • Chemical Communications, Vol. 51, Issue 28
  • DOI: 10.1039/C5CC00570A

A Modular and Size-Selective Synthesis of [n]Cycloparaphenylenes: A Step toward the Selective Synthesis of [n,n] Single-Walled Carbon Nanotubes
journal, November 2010

  • Omachi, Haruka; Matsuura, Sanae; Segawa, Yasutomo
  • Angewandte Chemie International Edition, Vol. 49, Issue 52
  • DOI: 10.1002/anie.201005734

Efficient room-temperature synthesis of a highly strained carbon nanohoop fragment of buckminsterfullerene
journal, March 2014

  • Evans, Paul J.; Darzi, Evan R.; Jasti, Ramesh
  • Nature Chemistry, Vol. 6, Issue 5
  • DOI: 10.1038/nchem.1888

Synthesis and characterization of a highly strained donor–acceptor nanohoop
journal, January 2016

  • Van Raden, J. M.; Darzi, E. R.; Zakharov, L. N.
  • Organic & Biomolecular Chemistry, Vol. 14, Issue 24
  • DOI: 10.1039/C6OB00133E

Thiophene-Based, Radial π-Conjugation: Synthesis, Structure, and Photophysical Properties of Cyclo-1,4-phenylene-2′,5′-thienylenes
journal, November 2014

  • Ito, Hideto; Mitamura, Yukari; Segawa, Yasutomo
  • Angewandte Chemie, Vol. 127, Issue 1
  • DOI: 10.1002/ange.201409389

Curved Oligophenylenes as Donors in Shape-Persistent Donor-Acceptor Macrocycles with Solvatofluorochromic Properties
journal, July 2015

  • Kuwabara, Takuya; Orii, Jun; Segawa, Yasutomo
  • Angewandte Chemie, Vol. 127, Issue 33
  • DOI: 10.1002/ange.201503397

    Works referencing / citing this record:

    CCDC 1834626: Experimental Crystal Structure Determination
    dataset, January 2018


    Giant Cyclo[ n ]thiophenes with Extended π Conjugation
    journal, August 2009

    • Zhang, Fan; Götz, Günther; Winkler, Henrik D. F.
    • Angewandte Chemie International Edition, Vol. 48, Issue 36
    • DOI: 10.1002/anie.200900101

    A Modular and Size-Selective Synthesis of [n]Cycloparaphenylenes: A Step toward the Selective Synthesis of [n,n] Single-Walled Carbon Nanotubes
    journal, November 2010

    • Omachi, Haruka; Matsuura, Sanae; Segawa, Yasutomo
    • Angewandte Chemie International Edition, Vol. 49, Issue 52
    • DOI: 10.1002/anie.201005734

    Conjugated Macrocycles: Concepts and Applications
    journal, September 2011

    • Iyoda, Masahiko; Yamakawa, Jun; Rahman, M. Jalilur
    • Angewandte Chemie International Edition, Vol. 50, Issue 45
    • DOI: 10.1002/anie.201006198

    Concise Synthesis and Crystal Structure of [12]Cycloparaphenylene
    journal, March 2011

    • Segawa, Yasutomo; Miyamoto, Shinpei; Omachi, Haruka
    • Angewandte Chemie International Edition, Vol. 50, Issue 14
    • DOI: 10.1002/anie.201007232

    Size-Selective Encapsulation of C60 by [10]Cycloparaphenylene: Formation of the Shortest Fullerene-Peapod
    journal, July 2011

    • Iwamoto, Takahiro; Watanabe, Yoshiki; Sadahiro, Tatsuya
    • Angewandte Chemie International Edition, Vol. 50, Issue 36
    • DOI: 10.1002/anie.201102302

    Size-Selective Complexation and Extraction of Endohedral Metallofullerenes with Cycloparaphenylene
    journal, February 2014

    • Nakanishi, Yusuke; Omachi, Haruka; Matsuura, Sanae
    • Angewandte Chemie International Edition, Vol. 53, Issue 12
    • DOI: 10.1002/anie.201311268

    Thiophene-Based, Radial π-Conjugation: Synthesis, Structure, and Photophysical Properties of Cyclo-1,4-phenylene-2′,5′-thienylenes
    journal, November 2014

    • Ito, Hideto; Mitamura, Yukari; Segawa, Yasutomo
    • Angewandte Chemie International Edition, Vol. 54, Issue 1
    • DOI: 10.1002/anie.201409389

    Curved Oligophenylenes as Donors in Shape-Persistent Donor-Acceptor Macrocycles with Solvatofluorochromic Properties
    journal, July 2015

    • Kuwabara, Takuya; Orii, Jun; Segawa, Yasutomo
    • Angewandte Chemie International Edition, Vol. 54, Issue 33
    • DOI: 10.1002/anie.201503397

    Atropisomerism in a Belt‐Persistent Nanohoop Molecule: Rotational Restriction Forced by Macrocyclic Ring Strain
    journal, March 2012

    • Hitosugi, Shunpei; Nakanishi, Waka; Isobe, Hiroyuki
    • Chemistry – An Asian Journal, Vol. 7, Issue 7
    • DOI: 10.1002/asia.201200187

    Size- and Orientation-Selective Encapsulation of C 70 by Cycloparaphenylenes
    journal, September 2013

    • Iwamoto, Takahiro; Watanabe, Yoshiki; Takaya, Hikaru
    • Chemistry - A European Journal, Vol. 19, Issue 42
    • DOI: 10.1002/chem.201302694

    Synthesis, Properties, and Design Principles of Donor–Acceptor Nanohoops
    journal, September 2015


    Synthesis of Cycloparaphenylenes and Related Carbon Nanorings: A Step toward the Controlled Synthesis of Carbon Nanotubes
    journal, May 2012

    • Omachi, Haruka; Segawa, Yasutomo; Itami, Kenichiro
    • Accounts of Chemical Research, Vol. 45, Issue 8
    • DOI: 10.1021/ar300055x

    Giant Macrocycles Composed of Thiophene, Acetylene, and Ethylene Building Blocks
    journal, December 2006

    • Nakao, Kazumi; Nishimura, Masayuki; Tamachi, Tomoya
    • Journal of the American Chemical Society, Vol. 128, Issue 51
    • DOI: 10.1021/ja067077t

    Selective and Random Syntheses of [ n ]Cycloparaphenylenes ( n = 8–13) and Size Dependence of Their Electronic Properties
    journal, June 2011

    • Iwamoto, Takahiro; Watanabe, Yoshiki; Sakamoto, Youichi
    • Journal of the American Chemical Society, Vol. 133, Issue 21
    • DOI: 10.1021/ja2020668

    Belt-Shaped π-Systems: Relating Geometry to Electronic Structure in a Six-Porphyrin Nanoring
    journal, November 2011

    • Sprafke, Johannes K.; Kondratuk, Dmitry V.; Wykes, Michael
    • Journal of the American Chemical Society, Vol. 133, Issue 43
    • DOI: 10.1021/ja2045919

    Highly Sensitive NH 3 Detection Based on Organic Field-Effect Transistors with Tris(pentafluorophenyl)borane as Receptor
    journal, September 2012

    • Huang, Weiguo; Besar, Kalpana; LeCover, Rachel
    • Journal of the American Chemical Society, Vol. 134, Issue 36
    • DOI: 10.1021/ja305287p

    Bottom-up Synthesis and Thread-in-Bead Structures of Finite ( n ,0)-Zigzag Single-Wall Carbon Nanotubes
    journal, July 2012

    • Hitosugi, Shunpei; Yamasaki, Takashi; Isobe, Hiroyuki
    • Journal of the American Chemical Society, Vol. 134, Issue 30
    • DOI: 10.1021/ja305723j

    Synthesis and Characterization of [5]Cycloparaphenylene
    journal, January 2014

    • Kayahara, Eiichi; Patel, Vijay Kumar; Yamago, Shigeru
    • Journal of the American Chemical Society, Vol. 136, Issue 6
    • DOI: 10.1021/ja413214q

    Cyclic 2,12-Porphyrinylene Nanorings as a Porphyrin Analogue of Cycloparaphenylenes
    journal, February 2015

    • Jiang, Hua-Wei; Tanaka, Takayuki; Mori, Hirotaka
    • Journal of the American Chemical Society, Vol. 137, Issue 6
    • DOI: 10.1021/ja513102m

    Synthesis, Characterization, and Theory of [9]-, [12]-, and [18]Cycloparaphenylene: Carbon Nanohoop Structures
    journal, December 2008

    • Jasti, Ramesh; Bhattacharjee, Joydeep; Neaton, Jeffrey B.
    • Journal of the American Chemical Society, Vol. 130, Issue 52
    • DOI: 10.1021/ja807126u

    Chiral Conjugated Corrals
    journal, July 2015

    • Ball, Melissa; Fowler, Brandon; Li, Panpan
    • Journal of the American Chemical Society, Vol. 137, Issue 31
    • DOI: 10.1021/jacs.5b05698

    Strain-Induced Stereoselective Formation of Blue-Emitting Cyclostilbenes
    journal, September 2015

    • Chen, Qishui; Trinh, M. Tuan; Paley, Daniel W.
    • Journal of the American Chemical Society, Vol. 137, Issue 38
    • DOI: 10.1021/jacs.5b06258

    Macrocyclization in the Design of Organic n-Type Electronic Materials
    journal, September 2016

    • Ball, Melissa; Zhong, Yu; Fowler, Brandon
    • Journal of the American Chemical Society, Vol. 138, Issue 39
    • DOI: 10.1021/jacs.6b05474

    Rigid, Conjugated Macrocycles for High Performance Organic Photodetectors
    journal, December 2016

    • Zhang, Boyuan; Trinh, M. Tuan; Fowler, Brandon
    • Journal of the American Chemical Society, Vol. 138, Issue 50
    • DOI: 10.1021/jacs.6b10276

    Fast Calculation of van der Waals Volume as a Sum of Atomic and Bond Contributions and Its Application to Drug Compounds
    journal, September 2003

    • Zhao, Yuan H.; Abraham, Michael H.; Zissimos, Andreas M.
    • The Journal of Organic Chemistry, Vol. 68, Issue 19
    • DOI: 10.1021/jo034808o

    Selective Synthesis and Crystal Structure of [10]Cycloparaphenylene
    journal, June 2012

    • Kayahara, Eiichi; Sakamoto, Yoichi; Suzuki, Toshiyasu
    • Organic Letters, Vol. 14, Issue 13
    • DOI: 10.1021/ol301242t

    Efficient room-temperature synthesis of a highly strained carbon nanohoop fragment of buckminsterfullerene
    journal, March 2014

    • Evans, Paul J.; Darzi, Evan R.; Jasti, Ramesh
    • Nature Chemistry, Vol. 6, Issue 5
    • DOI: 10.1038/nchem.1888

    Size-selective synthesis of [9]–[11] and [13]cycloparaphenylenes
    journal, January 2012

    • Ishii, Yuuki; Nakanishi, Yusuke; Omachi, Haruka
    • Chemical Science, Vol. 3, Issue 7
    • DOI: 10.1039/c2sc20343j

    The importance of intramolecular conductivity in three dimensional molecular solids
    journal, January 2019

    • Ball, Melissa L.; Zhang, Boyuan; Fu, Tianren
    • Chemical Science, Vol. 10, Issue 40
    • DOI: 10.1039/c9sc03144h

    Electronic sensing of vapors with organic transistors
    journal, April 2001

    • Crone, B.; Dodabalapur, A.; Gelperin, A.
    • Applied Physics Letters, Vol. 78, Issue 15
    • DOI: 10.1063/1.1360785

    [9]Cycloparaphenylene: Nickel-mediated Synthesis and Crystal Structure
    journal, April 2011

    • Segawa, Yasutomo; Šenel, Petr; Matsuura, Sanae
    • Chemistry Letters, Vol. 40, Issue 4
    • DOI: 10.1246/cl.2011.423

    The importance of intramolecular conductivity in three dimensional molecular solids
    journal, January 2019

    • Ball, Melissa L.; Zhang, Boyuan; Fu, Tianren
    • Chemical Science, Vol. 10, Issue 40
    • DOI: 10.1039/c9sc03144h

      Figures/Tables have been extracted from DOE-funded journal article accepted manuscripts.