Design and Properties of Intermediate-Sized Narrow Band-Gap Conjugated Molecules Relevant to Solution-Processed Organic Solar Cells

Liu, Xiaofeng; Sun, Yanming; Hsu, Ben B. Y.; Lorbach, Andreas; Qi, Li; Heeger, Alan J.; Bazan, Guillermo C.

Design and Properties of Intermediate-Sized Narrow Band-Gap Conjugated Molecules Relevant to Solution-Processed Organic Solar Cells

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Datum

2014

Autor:innen

Liu, Xiaofeng

Sun, Yanming

Hsu, Ben B. Y.

Lorbach, Andreas

Qi, Li

Heeger, Alan J.

Bazan, Guillermo C.

DOI (zitierfähiger Link)

https://doi.org/10.1021/ja413144u

Sammlungen

Chemie

Publikationstyp

Zeitschriftenartikel

Publikationsstatus

Published

Erschienen in

Journal of the American Chemical Society : JACS. 2014, 136(15), pp. 5697-5708. ISSN 0002-7863. eISSN 1520-5126. Available under: doi: 10.1021/ja413144u

Zusammenfassung

Increases in the molecular length of narrow band gap conjugated chromophores reveal potentially beneficial optical and electronic properties, thermal stabilities, and high power conversion efficiencies when integrated into optoelectronic devices, such as bulk heterojunction organic solar cells. With the objective of providing useful information for understanding the transition from small-sized molecules to polymers, as well as providing a general chemical design platform for extracting relationships between molecular structure and bulk properties, we set out to vary the electron affinity of the molecular backbone. Therefore, a series of donor (D)-acceptor (A) alternating narrow band gap conjugated chromophores were synthesized based on the general molecular frameworks: D¹-A¹-D²-A²-D²-A¹-D¹ and D¹-A¹-D²-A²-D²-A²-D²-A¹-D¹. When the central electron-accepting moiety (A²) was varied or modified, two classes of molecules could be compared. First, we showed that the alteration of one single electron-accepting group, while maintaining the shape of the molecular framework, can effectively impact the optical properties and energy levels of the molecules. DFT ground state structure optimizations show similar "U" shape conformations among these molecules. Second, we examined how the site-specific introduction of fluorine atom(s) modifies the thermal properties in the solid state, while maintaining relatively similar optical and electrochemical features of interest. Structure-property relationship of such molecular systems could be rationally evaluated in the aspects of thermal-responsive molecular organizations in the solid state and dipole moments both in the ground and excited states. The impact of molecular structure on charge carrier mobilities in field effect transistors and the performance of photovoltaic devices were also studied.

Fachgebiet (DDC)

540 Chemie

Zitieren

ISO 690

LIU, Xiaofeng, Yanming SUN, Ben B. Y. HSU, Andreas LORBACH, Li QI, Alan J. HEEGER, Guillermo C. BAZAN, 2014. Design and Properties of Intermediate-Sized Narrow Band-Gap Conjugated Molecules Relevant to Solution-Processed Organic Solar Cells. In: Journal of the American Chemical Society : JACS. 2014, 136(15), pp. 5697-5708. ISSN 0002-7863. eISSN 1520-5126. Available under: doi: 10.1021/ja413144u

BibTex

@article{Liu2014-04-16Desig-39248,
  year={2014},
  doi={10.1021/ja413144u},
  title={Design and Properties of Intermediate-Sized Narrow Band-Gap Conjugated Molecules Relevant to Solution-Processed Organic Solar Cells},
  number={15},
  volume={136},
  issn={0002-7863},
  journal={Journal of the American Chemical Society : JACS},
  pages={5697--5708},
  author={Liu, Xiaofeng and Sun, Yanming and Hsu, Ben B. Y. and Lorbach, Andreas and Qi, Li and Heeger, Alan J. and Bazan, Guillermo C.}
}

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    <dcterms:abstract xml:lang="eng">Increases in the molecular length of narrow band gap conjugated chromophores reveal potentially beneficial optical and electronic properties, thermal stabilities, and high power conversion efficiencies when integrated into optoelectronic devices, such as bulk heterojunction organic solar cells. With the objective of providing useful information for understanding the transition from small-sized molecules to polymers, as well as providing a general chemical design platform for extracting relationships between molecular structure and bulk properties, we set out to vary the electron affinity of the molecular backbone. Therefore, a series of donor (D)-acceptor (A) alternating narrow band gap conjugated chromophores were synthesized based on the general molecular frameworks: D&lt;sup&gt;1&lt;/sup&gt;-A&lt;sup&gt;1&lt;/sup&gt;-D&lt;sup&gt;2&lt;/sup&gt;-A&lt;sup&gt;2&lt;/sup&gt;-D&lt;sup&gt;2&lt;/sup&gt;-A&lt;sup&gt;1&lt;/sup&gt;-D&lt;sup&gt;1&lt;/sup&gt; and D&lt;sup&gt;1&lt;/sup&gt;-A&lt;sup&gt;1&lt;/sup&gt;-D&lt;sup&gt;2&lt;/sup&gt;-A&lt;sup&gt;2&lt;/sup&gt;-D&lt;sup&gt;2&lt;/sup&gt;-A&lt;sup&gt;2&lt;/sup&gt;-D&lt;sup&gt;2&lt;/sup&gt;-A&lt;sup&gt;1&lt;/sup&gt;-D&lt;sup&gt;1&lt;/sup&gt;. When the central electron-accepting moiety (A&lt;sup&gt;2&lt;/sup&gt;) was varied or modified, two classes of molecules could be compared. First, we showed that the alteration of one single electron-accepting group, while maintaining the shape of the molecular framework, can effectively impact the optical properties and energy levels of the molecules. DFT ground state structure optimizations show similar "U" shape conformations among these molecules. Second, we examined how the site-specific introduction of fluorine atom(s) modifies the thermal properties in the solid state, while maintaining relatively similar optical and electrochemical features of interest. Structure-property relationship of such molecular systems could be rationally evaluated in the aspects of thermal-responsive molecular organizations in the solid state and dipole moments both in the ground and excited states. The impact of molecular structure on charge carrier mobilities in field effect transistors and the performance of photovoltaic devices were also studied.</dcterms:abstract>
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