For this to work, you're going to need to know what the size of that image is. Then go into your template's entries.tpl (copy the one from the templates/default/ directory if your template doesn't have one) and find where the category icon is displayed:
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<span class="serendipity_entryIcon">
{foreach from=$entry.categories item="entry_category"}
{if $entry_category.category_icon}
<a href="{$entry_category.category_link}"><img class="serendipity_entryIcon" title="{$entry_category.category_name|@escape}{$entry_category.category_description|@emptyPrefix}" alt="{$entry_category.category_name|@escape}" src="{$entry_category.category_icon}" /></a>
{/if}
{/foreach}
</span>
That's inside a foreach loop that goes through each entry:
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{foreach from=$dategroup.entries item="entry"}
Change the foreach loop so it has a name:
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{foreach name="entryloop" from=$dategroup.entries item="entry"}
And you can check to see if this is the first entry, and make appropriate changes:
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{if $smarty.foreach.entryloop.first}
<span class="serendipity_entryBigIcon">
{else}
<span class="serendipity_entryIcon">
{/if}
{foreach from=$entry.categories item="entry_category"}
{if $entry_category.category_icon}
<a href="{$entry_category.category_link}"><img class="serendipity_entryIcon" title="{$entry_category.category_name|@escape}{$entry_category.category_description|@emptyPrefix}" alt="{$entry_category.category_name|@escape}" src="{$entry_category.category_icon}" /></a>
{/if}
{/foreach}
</span>
Finally, change the style.css (again, copy from templates/default if your template doesn't have one, but it ought to have one) and copy the lines for serendipity_entryIcon to serendipity_entryBigIcon and make the size larger.
Alternatively, if you make your own larger-size thumbnails, you can name them in some reliable fashion and replace the "{$entry_category.category_icon}" with "{$entry_category.category_icon}_big" or similar.