Synthesis of Organic Semiconductors - Revision history

128.95.39.187: /* Fluorinated pentacene */

2010-03-17T15:44:06Z

Fluorinated pentacene

← Older revision		Revision as of 08:44, 17 March 2010
Line 146:		Line 146:
	μ = 0.22 cm<sup>2</sup>/Vs and I<sub>on</sub>/I<sub>off</sub> =10<sup>5</sup>		μ = 0.22 cm<sup>2</sup>/Vs and I<sub>on</sub>/I<sub>off</sub> =10<sup>5</sup>

	see Y. Sakamoto; T. Suzukil; M. Kobayashi; Y. Gao; Y. Fukai; Y. Inoue; F. Sato; S. Tokito J. Am. Chem. Soc., 2004, 126, 8138–8140.		see Sakamoto 2004 <ref>Y. Sakamoto; T. Suzukil; M. Kobayashi; Y. Gao; Y. Fukai; Y. Inoue; F. Sato; S. Tokito J. Am. Chem. Soc., 2004, 126, 8138–8140</ref>.

	<br clear='all'>		<br clear='all'>

	==== C60 derivatives ====		==== C60 derivatives ====
	[[Image:PCBM.png\|thumb\|300px\|PCBM]]		[[Image:PCBM.png\|thumb\|300px\|PCBM]]

Cmditradmin: /* Examples of p-type molecules: Pentacene */

2010-03-12T00:23:22Z

Examples of p-type molecules: Pentacene

← Older revision		Revision as of 17:23, 11 March 2010
Line 63:		Line 63:
	Insoluble: Devices fabricated by vacuum sublimation		Insoluble: Devices fabricated by vacuum sublimation

	Pentacene is oxygen and light sensitive		Pentacene is oxygen and light-sensitive

	<br clear='all'>		<br clear='all'>

	=== Efforts to solubilize pentacene: Silyl modified pentacene ===		=== Efforts to solubilize pentacene: Silyl modified pentacene ===
	[[Image:Silyl_pentacene.png\|thumb\|500px\|Silyl modified pentacene]]		[[Image:Silyl_pentacene.png\|thumb\|500px\|Silyl modified pentacene]]

Cmditradmin at 22:53, 10 March 2010

2010-03-10T22:53:32Z

← Older revision		Revision as of 15:53, 10 March 2010
Line 1:		Line 1:
			<table id="toc" style="width: 100%">
			<tr>
			<td style="text-align: left; width: 33%">[[Organic Electronics Overview\|Previous Topic]]</td>
			<td style="text-align: center; width: 33%">[[Main_Page#Organic Electronics\|Return to Organic Electronics Menu]]</td>
			<td style="text-align: right; width: 33%">[[Organic Field Effect Transistors\|Next Topic]]</td>

			</tr>
			</table>

	== Design criteria ==		== Design criteria ==

Cmditradmin: /* Externally initiated P3HT synthesis */

2010-02-13T00:14:59Z

Externally initiated P3HT synthesis

← Older revision		Revision as of 17:14, 12 February 2010
Line 429:		Line 429:
	see Doubina and Luscombe 2009 <ref>Doubina and Luscombe, Macromolecules, 2009, 42, 7670</ref>		see Doubina and Luscombe 2009 <ref>Doubina and Luscombe, Macromolecules, 2009, 42, 7670</ref>

	~~adapting to ligands other than PPh3~~
	A novel method for the external initiated polymerizations of P3HT has developed by CMDITR researchers. The method produces a polymer with a well-defined molecular weight, narrow polydispersity index (PDI), 100% initiation efficiency, 100% regioregularity. This work represents the most control achieved for the synthesis of P3HT.

	~~see Bronstein and Luscombe 2009 <ref>H. Bronstein, C. K. Luscombe, J. Am. Chem. Soc., 2009, 131, 12894</ref>~~

	<br clear='all'>		<br clear='all'>
	[[Image:P3ht_synth_ext_ligand.png\|thumb\|300px\|]]		[[Image:P3ht_synth_ext_ligand.png\|thumb\|300px\|]]

	see van Leeuwen 2000 <ref>van Leeuwen et al. Chem. Rev. 2000, 100, 2741</ref>		see van Leeuwen 2000 <ref>van Leeuwen et al. Chem. Rev. 2000, 100, 2741</ref>
			<br clear='all'>

			=== Adapting to ligands other than PPh3 ===
			[[Image:P3ht_synth_regioregular.png\|thumb\|500px\|]]

			A novel method for the external initiated polymerizations of P3HT has developed by CMDITR researchers. The method produces a polymer with a well-defined molecular weight, narrow polydispersity index (PDI), 100% initiation efficiency, 100% regioregularity. This work represents the most control achieved for the synthesis of P3HT.

			see Bronstein and Luscombe 2009 <ref>H. Bronstein, C. K. Luscombe, J. Am. Chem. Soc., 2009, 131, 12894</ref>

	== References ==		== References ==
	<references/>		<references/>

Cmditradmin: /* Externally initiated P3HT synthesis */

2010-02-13T00:12:15Z

Externally initiated P3HT synthesis

← Older revision		Revision as of 17:12, 12 February 2010
Line 420:		Line 420:

	[[Image:P3ht_synth_ext2.png\|thumb\|500px\|]]		[[Image:P3ht_synth_ext2.png\|thumb\|500px\|]]
			<br clear='all'>
	TM = transmetallation		TM = transmetallation
	RE = reductive elimination		RE = reductive elimination
Line 433:		Line 433:

	see Bronstein and Luscombe 2009 <ref>H. Bronstein, C. K. Luscombe, J. Am. Chem. Soc., 2009, 131, 12894</ref>		see Bronstein and Luscombe 2009 <ref>H. Bronstein, C. K. Luscombe, J. Am. Chem. Soc., 2009, 131, 12894</ref>
			<br clear='all'>
			[[Image:P3ht_synth_ext_ligand.png\|thumb\|300px\|]]

			see van Leeuwen 2000 <ref>van Leeuwen et al. Chem. Rev. 2000, 100, 2741</ref>

	== References ==		== References ==
	<references/>		<references/>

Cmditradmin: /* Externally initiated P3HT synthesis */

2010-02-13T00:10:21Z

Externally initiated P3HT synthesis

← Older revision		Revision as of 17:10, 12 February 2010
Line 417:		Line 417:

	=== Externally initiated P3HT synthesis ===		=== Externally initiated P3HT synthesis ===
			[[Image:P3ht_synth_ext.png\|thumb\|500px\|]]

			[[Image:P3ht_synth_ext2.png\|thumb\|500px\|]]

	TM = transmetallation		TM = transmetallation
Line 424:		Line 427:
	Restricted to only being able to use PPh3 as a ligand. dppp gives H/Br polymer.		Restricted to only being able to use PPh3 as a ligand. dppp gives H/Br polymer.

	Doubina and Luscombe, Macromolecules, 2009, 42, 7670		see Doubina and Luscombe 2009 <ref>Doubina and Luscombe, Macromolecules, 2009, 42, 7670</ref>

	adapting to ligands other than PPh3		adapting to ligands other than PPh3
	A novel method for the external initiated polymerizations of P3HT has developed by CMDITR researchers. The method produces a polymer with a well-defined molecular weight, narrow polydispersity index (PDI), 100% initiation efficiency, 100% regioregularity. This work represents the most control achieved for the synthesis of P3HT.		A novel method for the external initiated polymerizations of P3HT has developed by CMDITR researchers. The method produces a polymer with a well-defined molecular weight, narrow polydispersity index (PDI), 100% initiation efficiency, 100% regioregularity. This work represents the most control achieved for the synthesis of P3HT.

	H. Bronstein, C. K. Luscombe, J. Am. Chem. Soc., 2009, 131, 12894		see Bronstein and Luscombe 2009 <ref>H. Bronstein, C. K. Luscombe, J. Am. Chem. Soc., 2009, 131, 12894</ref>

	== References ==		== References ==
	<references/>		<references/>

Cmditradmin: /* P3HT synthesis */

2010-02-13T00:06:21Z

P3HT synthesis

← Older revision		Revision as of 17:06, 12 February 2010
Line 396:		Line 396:

	When Ni(0) reductively eliminates, it can in theory reinsert into any Ar-Br bond. If this were to occur, this would be a step-growth polymerization		When Ni(0) reductively eliminates, it can in theory reinsert into any Ar-Br bond. If this were to occur, this would be a step-growth polymerization


			But McCullough and Yokozawa found that the resulting polymer had a narrow PDI and controlled molecular weight, which means that it is likely to be a chain-growth polymerization.
			[[Image:P3ht_synth2.png\|thumb\|500px\|P3HT synthesis]]

			dppp>dppe>dppf>PPh3

			Polymerization is heavily ligand dependent and works best if dppp is used as the ligand.
			*Narrow PDI
			*MW proportional to Ni loading

			Associated pair

			Key step: Ni(0) only adds into the same growing polymer chain resulting in chain-growth polymerization

			see McCullough <ref>McCullough, Macromolecules 2004, 37, 3526</ref>

			see Miyakoshi <ref>Miyakoshi and Yokozawa et al., J. Am. Chem. Soc. 2005, 127, 17542</ref>
			<br clear='all'>

	=== Externally initiated P3HT synthesis ===		=== Externally initiated P3HT synthesis ===

Cmditradmin: /* P3HT synthesis */

2010-02-13T00:02:08Z

P3HT synthesis

← Older revision		Revision as of 17:02, 12 February 2010
Line 392:		Line 392:

	=== P3HT synthesis ===		=== P3HT synthesis ===
			[[Image:P3ht_synth.png\|thumb\|500px\|P3HT synthesis]]
	P3HT synthesis was originally thought to occur via a step-growth polymerization.		P3HT synthesis was originally thought to occur via a step-growth polymerization.

	When Ni(0) reductively eliminates, it can in theory reinsert into any Ar-Br bond. If this were to occur, this would be a step-growth polymerization		When Ni(0) reductively eliminates, it can in theory reinsert into any Ar-Br bond. If this were to occur, this would be a step-growth polymerization


	=== Externally initiated P3HT synthesis ===		=== Externally initiated P3HT synthesis ===

Cmditradmin: /* Metal catalyzed cross-coupling polymerizations */

2010-02-13T00:01:16Z

Metal catalyzed cross-coupling polymerizations

← Older revision		Revision as of 17:01, 12 February 2010
Line 388:		Line 388:

	=== Metal catalyzed cross-coupling polymerizations ===		=== Metal catalyzed cross-coupling polymerizations ===
	The majority of conjugated polymers are synthesized via metal catalyzed cross-coupling reactions eg. Ni mediated reactions is shown ~~below~~.		[[Image:Crosscoupling.png\|thumb\|400px\|]]
			The majority of conjugated polymers are synthesized via metal catalyzed cross-coupling reactions eg. Ni mediated reactions is shown.

	=== P3HT synthesis ===		=== P3HT synthesis ===

Cmditradmin: /* Ambipolar polymers */

2010-02-12T23:59:39Z

Ambipolar polymers

← Older revision		Revision as of 16:59, 12 February 2010
Line 376:		Line 376:
	=== Ambipolar polymers ===		=== Ambipolar polymers ===

	F. ~~S. Kim and S. A. Jenekhe et al. Adv. Mater., Vol. 21, P. 1-5, 2009~~		[[Image:Ambipolar.png\|thumb\|500px\|]]

			μh = 10-3 cm2/(V s)
			μe = 10-2 cm2/(V s)


			see Kim and Jenekhe 2009 <ref>F. S. Kim and S. A. Jenekhe et al. Adv. Mater., Vol. 21, P. 1-5, 2009</ref>
			<br clear='all'>

	== Controlled polymer synthesis ==		== Controlled polymer synthesis ==